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All Forum Posts by: Shaylynn O'Leary

Shaylynn O'Leary has started 6 posts and replied 23 times.

Post: Help Picking an OOS Market- My story below

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40
Quote from @Kerlous Tadres:
Quote from @Shaylynn O'Leary:

I need help picking an OOS market. Let me tell you my back story. I live in Central Oregon where the median home price is approximately $725k. I have recently obtained a property off market that we’re flipping and wanting to reinvest most of the proceeds into an OOS market that is more affordable. We are not interested in owning rentals in Oregon, only flipping.

Our goal is to have a small but mighty portfolio, much like Chad Carson’s model he describes in his book and podcast. We want to use proceeds from our flips here in Central Oregon to acquire and eventually pay off properties in a more affordable market.

We prefer multifamily properties where we will do a mix of MTR & LTR, but also open to SF. The properties do not have to cash flow a significant amount (although I wouldn’t hate that) they just have to sustain themselves as we have three incomes between us and not looking to quit our W2’s to live off cash flow.

My problem: I’m having a hard time picking a market that meets my goals. Some markets I have considered are:

  • St. Louis, Mo
  • Kansas City, MO
  • Indianapolis, IN
  • Dayton, OH
  • Raleigh (area), NC

I would appreciate any insight and time anyone is willing to give. Thank you.


 Dayton, OH is a great ltr area with pretty good cash-flow

@Kerlous Tadres

 Hi Kerlous! Thanks for responding. Can you share why you think it's great? I'm curious because I always cirlce back around to Dayton. Thank you!

Post: Help Picking an OOS Market- My story below

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40

I need help picking an OOS market. Let me tell you my back story. I live in Central Oregon where the median home price is approximately $725k. I have recently obtained a property off market that we’re flipping and wanting to reinvest most of the proceeds into an OOS market that is more affordable. We are not interested in owning rentals in Oregon, only flipping.

Our goal is to have a small but mighty portfolio, much like Chad Carson’s model he describes in his book and podcast. We want to use proceeds from our flips here in Central Oregon to acquire and eventually pay off properties in a more affordable market.

We prefer multifamily properties where we will do a mix of MTR & LTR, but also open to SF. The properties do not have to cash flow a significant amount (although I wouldn’t hate that) they just have to sustain themselves as we have three incomes between us and not looking to quit our W2’s to live off cash flow.

My problem: I’m having a hard time picking a market that meets my goals. Some markets I have considered are:

  • St. Louis, Mo
  • Kansas City, MO
  • Indianapolis, IN
  • Dayton, OH
  • Raleigh (area), NC

I would appreciate any insight and time anyone is willing to give. Thank you.

Post: What do you know about investing in Indianapolis & Surrounding Areas

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40

Thank you for your help and insight. Much appreciated!

Post: What do you know about investing in Indianapolis & Surrounding Areas

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40

I'm an OOS investor looking to deploy my capital in Indianapolis and surrounding areas. I'm looking for properties that I can combine STR/MTR but they also must cashflow (at least a little) at a LTR. Also looking at LTR for surrounding areas specifically.

Looking for any and all insight from anyone who has experience in this market. Thank you for your time!

Post: Advice: New Investor/Small but Mighty Portfolio/ Long Term Game Plan

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40
Quote from @Jaycee Greene:

@Shaylynn O'Leary well, that's at least someone with "eyes and ears" in the actual market. 

What type of properties are you looking to add to your portfolio? SF and 2-4 MF assume? And is your purchase price target $150k, or is that the amount of equity you have to invest? And are you looking for turn-key properties or something along the lines of a "fixer upper"?


That is very true! I think starting out SF and then moving to small MF. My target purchase price is ideally under $150k as my long term goal is to pay them off as quickly as possible. I would like them to cash flow at least $150 a month just so the property sustains itself. The cash flow will be reinvested into the property in some capacity. I'm not looking to replace my w2 income with it.  I'm mostly interested in the long term gratification when the properties are owned free and clear. Since it will be out of state, I'm looking for mostly turn key or just cosmetic fixers. 

Post: Advice: New Investor/Small but Mighty Portfolio/ Long Term Game Plan

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40

@Jaycee Greene no connections except for connecting with one realtor in St. Louis this last spring. 

Post: Advice: New Investor/Small but Mighty Portfolio/ Long Term Game Plan

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40

Hello, I' m a newer investor in the process of getting my first property under contract near where I currently live. I live in a good, appreciating market where the average home price is above $700,000. Not a great cash flowing market. The state that I live in is also not landlord friendly.  My plan is to have a small but mighty real estate portfolio, much like Chad Carson's book. I want to use the profits from flipping in my home market to obtain and pay off properties in a better cash flowing, landlord friendly market. Initially, the properties that I buy in another market don't have to cash flow a lot, my metric is $150, as I'm focused on the long term gain when they're paid off  and I have a W2 and am also a realtor. I'm not looking to leave my W2 tomorrow.  However, my hold up is what market to look at that will help me meet my goals. I have looked into these markets: St. Louis, MO, Indianapolis IN, Columbus OH, Cincinnati OH, and Columbia SC. Does anyone have any advice on which direction to go? Thank you!

Post: If you had one question for a professional house flipper, what would it be??

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40

I am currently looking at my first investment property. The property needs to be rehabbed. Initially we thought we would flip, but now we're thinking of holding and using the equity for future investments. What formula or criteria do you use to decide whether to flip or to hold? I'm interested in hearing different perspectives. Thank you

Post: Fix & Flip or Buy& Hold??

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40
Quote from @Jaycee Greene:

Much of that decision is based on what you want to get in $ profit or % return. I'm happy to help walk you through the process if you want.


 Thank you, Jaycee! I would appreciate any help!

Post: Fix & Flip or Buy& Hold??

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 23
  • Votes 40
Quote from @Ryan Irwin:
Quote from @Shaylynn O'Leary:


Yes, the property will cashflow! We are leaning towards holding it and doing a refi to deploy capital on future projects. My long term goal is to have the "smally but mighty" portfolio and pay off properties as quickly as possible. I have a W2, so the extra rental income would be reinvetsed into the property. Thanks for your response!


Agree on the above. I'm actually doing this right now and am going to hold a recent flip project as the area is going to be developed over the next couple of years and I expect appreciation to rise. I'm doing a cash out DSCR refi so I still get some of my capital back and can take advantage of cash flow/depreciation and all the other benefits of holding. However, if you can flip it and make a solid profit higher than what you would get out of a cash out refi and/or rents won't cash flow, then flipping makes good sense (unless you need a tax write off but since this is your first investment, that probably isn't the case).