Self Managing My last 30-Units

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Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Alfath Ahmed:

Quote from @Shawn Ackerman:

After a decade of investing in the Milwaukee market from New York, I have officially liquidated my portfolio, scaling down from 88 units to 4. While the majority were sold, 15 were lost to foreclosure—a difficult but valuable lesson in this business.

My journey with out-of-state investing taught me a great deal about the trade-offs of self-management. While I saved on management fees, the time investment was significant. My remote team consisted of myself, a virtual assistant, and a network of independent contractors for repairs and on-site support. I transitioned to self-management after realizing my previous property management company was consistently overcharging me for turnovers and renovations.

Looking back, I would do it again, but I would exclusively target rent-to-own or commercial tenants. For those currently investing or considering it, here are my key takeaways:

1. Systems are everything: Documenting processes is the only way to make your operations truly replicable and efficient.

2. Delegate wisely: Hiring specialized contractors for specific tasks reduces overlap and streamlines operations.

3. Own your data: Always control the software platform used for tenant communication and documentation. If you part ways with a management company, you don’t want them holding your records hostage.

Milwaukee remains a market with excellent growth potential if the right strategy is applied. I’m closing this chapter, but I’m happy to answer any questions you have about my experience or the process of scaling down or investing Out of state.

Super valuable lessons! I'm managing my own portfolio in columbus and have been building systems to make it more efficient and systematic. Would love to connect.

Hey Alfath, Seems like you are locked in. Gotta love the mid-west markets. I'm here man. Hit me up. All the best to you and keep killing it.
0 Reply

Jimmy LieuBusiness Member

Real Estate Agent · Columbus, OH · Member since 2019 · 3k+ posts · 2k+ votes

2mo

Quote from @Shawn Ackerman:

After a decade of investing in the Milwaukee market from New York, I have officially liquidated my portfolio, scaling down from 88 units to 4. While the majority were sold, 15 were lost to foreclosure—a difficult but valuable lesson in this business.

My journey with out-of-state investing taught me a great deal about the trade-offs of self-management. While I saved on management fees, the time investment was significant. My remote team consisted of myself, a virtual assistant, and a network of independent contractors for repairs and on-site support. I transitioned to self-management after realizing my previous property management company was consistently overcharging me for turnovers and renovations.

Looking back, I would do it again, but I would exclusively target rent-to-own or commercial tenants. For those currently investing or considering it, here are my key takeaways:

1. Systems are everything: Documenting processes is the only way to make your operations truly replicable and efficient.

2. Delegate wisely: Hiring specialized contractors for specific tasks reduces overlap and streamlines operations.

3. Own your data: Always control the software platform used for tenant communication and documentation. If you part ways with a management company, you don’t want them holding your records hostage.

Milwaukee remains a market with excellent growth potential if the right strategy is applied. I’m closing this chapter, but I’m happy to answer any questions you have about my experience or the process of scaling down or investing Out of state.

Great post, Shawn, and thanks for sharing both the wins and the challenges. Scaling to 88 units from out of state is no small feat, and I think your point about owning your systems is one that doesn't get talked about enough. I've found that having all leases, maintenance history, tenant communication, and financial records under your own control makes transitions much smoother, whether you're changing property managers or bringing management in-house. I'm also curious, after everything you experienced, what would you say was the biggest sign that a property manager wasn't the right fit before the overcharging became obvious? Thanks again for sharing your experience. Happy to connect and answer any questions you have!

Jimmy Lieu, Red 1 Realty4.9120 Reviews

2 Reply

Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Jimmy Lieu:

Quote from @Shawn Ackerman:

After a decade of investing in the Milwaukee market from New York, I have officially liquidated my portfolio, scaling down from 88 units to 4. While the majority were sold, 15 were lost to foreclosure—a difficult but valuable lesson in this business.

My journey with out-of-state investing taught me a great deal about the trade-offs of self-management. While I saved on management fees, the time investment was significant. My remote team consisted of myself, a virtual assistant, and a network of independent contractors for repairs and on-site support. I transitioned to self-management after realizing my previous property management company was consistently overcharging me for turnovers and renovations.

Looking back, I would do it again, but I would exclusively target rent-to-own or commercial tenants. For those currently investing or considering it, here are my key takeaways:

1. Systems are everything: Documenting processes is the only way to make your operations truly replicable and efficient.

2. Delegate wisely: Hiring specialized contractors for specific tasks reduces overlap and streamlines operations.

3. Own your data: Always control the software platform used for tenant communication and documentation. If you part ways with a management company, you don’t want them holding your records hostage.

Milwaukee remains a market with excellent growth potential if the right strategy is applied. I’m closing this chapter, but I’m happy to answer any questions you have about my experience or the process of scaling down or investing Out of state.
Great post, Shawn, and thanks for sharing both the wins and the challenges. Scaling to 88 units from out of state is no small feat, and I think your point about owning your systems is one that doesn't get talked about enough. I've found that having all leases, maintenance history, tenant communication, and financial records under your own control makes transitions much smoother, whether you're changing property managers or bringing management in-house. I'm also curious, after everything you experienced, what would you say was the biggest sign that a property manager wasn't the right fit before the overcharging became obvious? Thanks again for sharing your experience. Happy to connect and answer any questions you have!

Hi Jimmy, thanks for the kind words! Honestly, I turned a blind eye to the issues for too long, but looking back, the biggest red flag was a lack of partnership. My management company consistently tried to act as the "boss" rather than a service provider, which created a major control issue.

The clearest warning signs included:

* Blanket renovation pricing: Labor and materials were always lumped together, preventing true cost analysis.
* Excessive maintenance: Frequent repair requests were often initiated by management without tenant input or necessity.
* "Quick-to-evict" mentality: There was a lack of effort to resolve minor tenant issues before escalating to eviction.
* Financial friction: A clear preference for cash-paying tenants over program tenants, likely because the latter paid me directly, bypassing their potential control over funds.
* Lack of a united front: Management occasionally undermined my authority to the tenants rather than maintaining professional alignment.
* Opaque contracting: They favored specific vendors exclusively and rarely provided multiple estimates for larger jobs.

The list goes on, but those were the definitive indicators that the management team was not aligned with my long-term interests as an owner.
0 Reply

Clare PitcherBusiness Member

Property Manager · Milwaukee, WI · Member since 2024 · 162 posts · 97 votes

2mo

Great insights and advice. So sorry to hear you had a poor experience with property management. If you're ever looking to discuss the Milwaukee market or need help with any of your properties, please reach out.

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Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Clare Pitcher:

Great insights and advice. So sorry to hear you had a poor experience with property management. If you're ever looking to discuss the Milwaukee market or need help with any of your properties, please reach out.

It is a pleasure to meet you as well! I am currently in the process of decompressing, but I anticipate looking to start holding again sometime next year. I truly appreciate your offer and will certainly keep your contact information on hand for the many out-of-state investors I work with.

To be transparent, I previously held properties in the 53206, 53208, 53216, and 53210 zip codes. Please let me know if there are specific areas where you do not operate, as the investors purchasing our off-market deals are typically looking for cash flow and often gravitate toward C-D class assets.
1 Reply

Garrett CrosbyPro Member

Real Estate Agent · Los Angeles, United States · Member since 2021 · 392 posts · 162 votes

2mo

Shawn, respect for laying this out so honestly - most people only post the win, not the 15 units lost to foreclosure along the way. That's the real lesson for anyone reading this thread.

I invest out of state myself (I'm LA-based, hold buy & holds in Fayetteville, NC) and self-managing remotely taught me the same three things you listed, especially owning your own data. I switched software once specifically so I'd never be locked out of my own tenant history and maintenance records again.

The other thing I'd add: build your systems around your worst month, not your average one. Turnovers, a bad tenant, or a slow season will expose any gaps in your process fast when you're not local. Sounds like you already learned that the hard way, but it's worth spelling out for people newer to out-of-state investing reading this.

Appreciate you sharing the numbers, not just the highlight reel. That's rare on here.

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Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Garrett Crosby:

Shawn, respect for laying this out so honestly - most people only post the win, not the 15 units lost to foreclosure along the way. That's the real lesson for anyone reading this thread.
I invest out of state myself (I'm LA-based, hold buy & holds in Fayetteville, NC) and self-managing remotely taught me the same three things you listed, especially owning your own data. I switched software once specifically so I'd never be locked out of my own tenant history and maintenance records again.
The other thing I'd add: build your systems around your worst month, not your average one. Turnovers, a bad tenant, or a slow season will expose any gaps in your process fast when you're not local. Sounds like you already learned that the hard way, but it's worth spelling out for people newer to out-of-state investing reading this.
Appreciate you sharing the numbers, not just the highlight reel. That's rare on here.

Hey Garrett, spoken like a true veteran—spot on. We have to keep it real for those coming up behind us. I’m not ashamed of the foreclosures because there were valuable lessons in every single one of them, though honestly, losing my 10-unit building was the most painful one to swallow.

But that’s the reality of this business; stay in the game long enough and you’re bound to take an "L" or two. I really appreciate you adding your perspective to the thread!
0 Reply

J CastroBusiness Member

Lender · Florida · Member since 2025 · 673 posts · 240 votes

2mo

Quote from @Shawn Ackerman:

After a decade of investing in the Milwaukee market from New York, I have officially liquidated my portfolio, scaling down from 88 units to 4. While the majority were sold, 15 were lost to foreclosure—a difficult but valuable lesson in this business.

My journey with out-of-state investing taught me a great deal about the trade-offs of self-management. While I saved on management fees, the time investment was significant. My remote team consisted of myself, a virtual assistant, and a network of independent contractors for repairs and on-site support. I transitioned to self-management after realizing my previous property management company was consistently overcharging me for turnovers and renovations.

Looking back, I would do it again, but I would exclusively target rent-to-own or commercial tenants. For those currently investing or considering it, here are my key takeaways:

1. Systems are everything: Documenting processes is the only way to make your operations truly replicable and efficient.

2. Delegate wisely: Hiring specialized contractors for specific tasks reduces overlap and streamlines operations.

3. Own your data: Always control the software platform used for tenant communication and documentation. If you part ways with a management company, you don’t want them holding your records hostage.

Milwaukee remains a market with excellent growth potential if the right strategy is applied. I’m closing this chapter, but I’m happy to answer any questions you have about my experience or the process of scaling down or investing Out of state.

Thanks for sharing your journey, Shawn. There's a lot of valuable insight here, especially your point that systems are everything. Whether you're self-managing or using a property manager, having documented processes and maintaining control of your data can make a huge difference.

It's also a good reminder that real estate investing isn't always a straight path. Being transparent about both the successes and the setbacks provides valuable perspective for other investors.

Best of luck with your next chapter. I'm sure the lessons you've learned from managing an out-of-state portfolio will continue to pay dividends. Thanks for sharing your experience.

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Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @J Castro:

Quote from @Shawn Ackerman:

After a decade of investing in the Milwaukee market from New York, I have officially liquidated my portfolio, scaling down from 88 units to 4. While the majority were sold, 15 were lost to foreclosure—a difficult but valuable lesson in this business.

My journey with out-of-state investing taught me a great deal about the trade-offs of self-management. While I saved on management fees, the time investment was significant. My remote team consisted of myself, a virtual assistant, and a network of independent contractors for repairs and on-site support. I transitioned to self-management after realizing my previous property management company was consistently overcharging me for turnovers and renovations.

Looking back, I would do it again, but I would exclusively target rent-to-own or commercial tenants. For those currently investing or considering it, here are my key takeaways:

1. Systems are everything: Documenting processes is the only way to make your operations truly replicable and efficient.

2. Delegate wisely: Hiring specialized contractors for specific tasks reduces overlap and streamlines operations.

3. Own your data: Always control the software platform used for tenant communication and documentation. If you part ways with a management company, you don’t want them holding your records hostage.

Milwaukee remains a market with excellent growth potential if the right strategy is applied. I’m closing this chapter, but I’m happy to answer any questions you have about my experience or the process of scaling down or investing Out of state.

Thanks for sharing your journey, Shawn. There's a lot of valuable insight here, especially your point that systems are everything. Whether you're self-managing or using a property manager, having documented processes and maintaining control of your data can make a huge difference.
It's also a good reminder that real estate investing isn't always a straight path. Being transparent about both the successes and the setbacks provides valuable perspective for other investors.
Best of luck with your next chapter. I'm sure the lessons you've learned from managing an out-of-state portfolio will continue to pay dividends. Thanks for sharing your experience.

Hey J, I really appreciate you contributing to the thread. I’ve always believed in keeping it real— I don’t view those setbacks as losses, but as essential lessons. You can bet that the next chapter will be even stronger than the last. Thanks for the support!
0 Reply
J CastroBusiness Member
Lender · Florida · Member since 2025 · 673 posts · 240 votes
2mo
Quote from @Shawn Ackerman:

Quote from @J Castro:

Quote from @Shawn Ackerman:

After a decade of investing in the Milwaukee market from New York, I have officially liquidated my portfolio, scaling down from 88 units to 4. While the majority were sold, 15 were lost to foreclosure—a difficult but valuable lesson in this business.

My journey with out-of-state investing taught me a great deal about the trade-offs of self-management. While I saved on management fees, the time investment was significant. My remote team consisted of myself, a virtual assistant, and a network of independent contractors for repairs and on-site support. I transitioned to self-management after realizing my previous property management company was consistently overcharging me for turnovers and renovations.

Looking back, I would do it again, but I would exclusively target rent-to-own or commercial tenants. For those currently investing or considering it, here are my key takeaways:

1. Systems are everything: Documenting processes is the only way to make your operations truly replicable and efficient.

2. Delegate wisely: Hiring specialized contractors for specific tasks reduces overlap and streamlines operations.

3. Own your data: Always control the software platform used for tenant communication and documentation. If you part ways with a management company, you don’t want them holding your records hostage.

Milwaukee remains a market with excellent growth potential if the right strategy is applied. I’m closing this chapter, but I’m happy to answer any questions you have about my experience or the process of scaling down or investing Out of state.

Thanks for sharing your journey, Shawn. There's a lot of valuable insight here, especially your point that systems are everything. Whether you're self-managing or using a property manager, having documented processes and maintaining control of your data can make a huge difference.
It's also a good reminder that real estate investing isn't always a straight path. Being transparent about both the successes and the setbacks provides valuable perspective for other investors.
Best of luck with your next chapter. I'm sure the lessons you've learned from managing an out-of-state portfolio will continue to pay dividends. Thanks for sharing your experience.

Hey J, I really appreciate you contributing to the thread. I’ve always believed in keeping it real— I don’t view those setbacks as losses, but as essential lessons. You can bet that the next chapter will be even stronger than the last. Thanks for the support!

Absolutely! That's the mindset that separates successful investors from everyone else. Every experienced investor has a story of deals that didn't go as planned, but the lessons learned are often worth more than the profits from the easy ones.
I have no doubt your next chapter will be even stronger. Wishing you continued success, and thanks again for sharing your journey so openly—it provides valuable perspective for the rest of us.
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Shiloh LundahlPro Member

Rental Property Investor · Gilbert, AZ · Member since 2016 · 3k+ posts · 4k+ votes

2mo

@Shawn Ackerman hey man, I'm not sure if you're the same Shawn Ackerman that I would talk with back in the day on clubhouse or not, but thank you for sharing your story. The last 4 years have been very different in real estate for me compared to the previous 12. I felt the stress of possibly losing some properties so I can relate to that stress.

I think the things that have helped me with self-managing a similarly large portfolio was doing lease options or rent-to-own. And also having an assistant. Without those two aspects of my business, I don't think I would have been able to manager my portfolio and still have a therapy practice.

Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Shiloh Lundahl:

@Shawn Ackerman hey man, I'm not sure if you're the same Shawn Ackerman that I would talk with back in the day on clubhouse or not, but thank you for sharing your story. The last 4 years have been very different in real estate for me compared to the previous 12. I felt the stress of possibly losing some properties so I can relate to that stress.

I think the things that have helped me with self-managing a similarly large portfolio was doing lease options or rent-to-own. And also having an assistant. Without those two aspects of my business, I don't think I would have been able to manager my portfolio and still have a therapy practice.

LESSSSSSSSSGOOOOOOOOOO!!!!!!! What's the word my guy? Man, time flies. We were definitely in them CH streets lol.
Great points on the LO RO play. I have two of those left and a few mortgage notes. And when I start the rebuild it will be with that strategy and or commercial mixed use assets. The demand for day cares in that market is nuts!
I am glad to see you are doing well man. Let's stay in touch. All the best to you!
0 Reply

Jessica E.

Property Manager · South Bend, IN · Member since 2026 · 2 posts · 1 vote

2mo

Extremely valuable advice! Implementing systems and building a good team are vital to successful property management.

Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Jessica E.:

Extremely valuable advice! Implementing systems and building a good team are vital to successful property management.

Well said!!! I want to thank you for contributing to this thread Jessica. Greatly appreciated.
1 Reply

Eduardo Cavasotti

Investor · Charleston, SC · Member since 2018 · 195 posts · 82 votes

2mo

Shawn, the data point is the part most investors underestimate. The PM relationship can fail, but the real damage is when invoices, tenant history, owner statements, and vendor notes live inside their portal instead of yours. Full disclosure, I am founder/operator at DoorVault, the AI asset manager for investors who use PMs. DoorVault keeps the PM statement, bank tie out, documents, repair evidence, and manager grade in one owner system, so replacing a PM does not mean rebuilding the portfolio from email scraps.

[email protected]941-914-7779

Ashish AcharyaBusiness Member

CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes

2mo

That's a lot to have gone through, 15 foreclosures out of 88 units is a genuinely tough outcome to work through. Worth flagging for anyone reading this: foreclosure counts as a deemed sale for tax purposes, so each one likely triggered its own gain or loss, and if any debt got forgiven along the way, that's separate cancellation of debt income stacked on top, two tax events on one transaction. With 15 of these, I'd want to double check each got reported correctly, especially if any 1099-A or 1099-C showed up late. On the properties you sold, if cost seg was ever done on them, make sure recapture was calculated right too, that's easy to miss when a portfolio's wound down over years instead of all at once. Really appreciate you being this transparent about the numbers, foreclosure doesn't come up enough in these threads. Happy to connect!

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Garrett CrosbyPro Member

Real Estate Agent · Los Angeles, United States · Member since 2021 · 392 posts · 162 votes

2mo

Shawn, wishing you a smooth reset this year. You clearly know what you're doing — 15 foreclosures out of 88 is a rough stat to post publicly, and most people wouldn't. Whatever you rebuild toward next, the lessons you laid out here will save someone a lot of pain. Feel free to reach out anytime if you want to compare notes on the rebuild.

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Shawn AckermanPro Member
OP
Real Estate Entrepreneur · Mid West, East Coast · Member since 2015 · 3k+ posts · 1k+ votes
2mo
Quote from @Garrett Crosby:

Shawn, wishing you a smooth reset this year. You clearly know what you're doing — 15 foreclosures out of 88 is a rough stat to post publicly, and most people wouldn't. Whatever you rebuild toward next, the lessons you laid out here will save someone a lot of pain. Feel free to reach out anytime if you want to compare notes on the rebuild.

Thanks for the support, Garrett. To clarify, it was 3 foreclosures total, though those accounted for 15 units (a 10-unit, a 4-unit, and a single-family home). I’m currently in "mental health mode," focusing on family time and traveling for the next 6-8 months. I’ll definitely rebuild bigger and better when the time is right, but for now, I’m just enjoying the peace.
0 Reply

Andre Brock

Investor · Cleveland, OH · Member since 2013 · 120 posts · 77 votes

2mo

Thanks Shawn for sharing your story it’s inspiring on how you went into a new market with so much uncertainty but seen the plan through much continued success in your journey.