All Forum Posts by: Brooke Melton

@JJ P.  Thanks so much for this — it really makes a lot of sense. I’ve just found a new tenant, so I’m going to hold off a bit before offloading. Still, your response gave me a lot of reassurance in the direction I was already leaning.

Thanks, @Chris Seveney. Oregon is definitely a unique beast, and being a landlord in Portland has been challenging enough—so I truly appreciate your insights, especially as they relate to this market.

This is incredibly helpful, @Dave Foster—thank you for generously sharing your knowledge! I’ll definitely be looking into this further and may reach out as I dive deeper into 1031 exchanges.

Thanks, @Ryan Spath! I really appreciate the way you laid this out—lots of good food for thought.

I’ll admit, I get a little nervous about making big investments. I’ve been considering dividing up the capital to invest in a couple of properties instead of just one. I live in a market that’s wildly expensive, but I’ve watched my own home nearly double in value over the past eight years. So yes, I completely agree—if you’re in the right market with the right timing, the gains can be significant. I will give this more consideration.

And I’m with you—no condos for me either, and ideally no HOAs. This condo was actually my very first home purchase from years ago. I only held on because it was easy to manage and still cash flowing. 😉

@Ryan Spathundefined

Thanks, Jared! I definitely have no interest in purchasing condos (or any other SFHs with an HOA) moving forward. That condo was my first "adult" home purchase and happened to work well as a rental for a while, but when it comes to current and future investments, avoiding HOAs is now one of my top criteria.

My second home purchase—also now a rental—does have a neighborhood HOA, but I've been fortunate. The VP of the HOA is relatively young and owns two homes in the community that she operates as STRs. As long as she's on the board, it looks like STRs will remain permitted, which gives me some peace of mind.

I recently acquired a residential multifamily property and plan to stick with those and SFHs in cash-flowing markets going forward. Right now, I’m really weighing the pros and cons of seller financing with a longer-term payout versus doing a 1031 exchange—particularly when it comes to tax implications and overall lifestyle alignment. Seller financing could offer a smoother transition and potentially a higher price point, while also saving on agent commissions and minimizing vacancy risk. On the other hand, a 1031 has the benefit of deferring taxes, but comes with a stricter timeline and the risk of losing rental income during the sale and reinvestment process.

Oh, and I do not own the property outright, but the buyer would pay off the loan with the down payment. 

I really appreciate the insight you’ve shared—lots to think about!

I purchased a condo in Portland back in 2005. I lived in it for a few years before renting it out when I moved away for grad school. Over the years, the property has consistently cash flowed—and at times, quite significantly—up until recently.

Unfortunately, the Portland riots impacted the rental market, and local rents dropped. My unit, which used to rent for $2,100, is renting for $1,800. On top of that, HOA fees recently jumped by nearly $200/month—bringing the total to $649—which has completely wiped out the little cash flow I had left. I still owe about $64K on the loan, and the property is currently worth around $360K. Condos in the area aren't moving quickly, and holding the property without a tenant could become expensive fast.

Just the other day, I got a call from an investor who expressed interest in buying. They initially mentioned a subject-to deal and then pivoted to owner financing. I’ve never done seller financing—on either side of a deal—so this is new territory for me. I typically stick to more conventional strategies, but I’ll admit I’m intrigued. Skipping agent commissions and redirecting some of that savings toward a strong legal team to handle the paperwork sounds like a smart tradeoff.

That said, I’m still in the exploratory phase. My original plan was to do a 1031 exchange and roll the equity into two other investments. I do have the cash to fund those without using a 1031, but I liked the idea of reallocating the equity without tapping into my brokerage or money market accounts.

I know there are risks with seller financing, but I’d love to hear from those with firsthand experience—what worked well, what didn’t, and what unexpected lessons you learned along the way. Any insight would be much appreciated!

I'm a relatively new investor in the grand scheme of things, but I wanted to share a personal story that might offer some perspective.

I bought a property back in 2007 that was listed at $300K and got it for $250K—what felt like a great deal at the time. But by 2008, the value had dropped by almost $50K. It was tough to see, and it took quite a while for prices to bounce back.

Luckily, the property stayed cash-flow positive through the years. I eventually furnished it, which significantly increased the rental income, and now I use it as a short-term rental (Airbnb). That setup allows me to enjoy the property when I want, still earn income, and take advantage of tax write-offs.

I’m really glad I held onto it. I learned a lot—especially after my first property manager disappeared and later filed for bankruptcy, which cost me several months of rent and two deposits. After that, I decided to self-manage, and it was honestly the best thing I could’ve done.

If you’re feeling discouraged, my advice is to explore ways to pivot: furnish the space, try a different rental model (mid- or short-term), or work on strategies to keep good tenants longer. Real estate rewards patience. Over time—and depending on your market—you’ll likely see growth in both rental income and property value. Hang in there.

Hey Chris,

I totally feel your pain—I'm based in Santa Barbara, CA, where the median home price is over 5 times the national average. It's overwhelming to even think about making million-dollar investments right out of the gate.

Fortunately, I moved around a bit when I was younger and bought homes that are now rentals. It's definitely possible to manage properties from out of state (at least for your first couple), or hire a property manager to help out. That said, the first management company I hired went MIA within a year, so I started managing my own properties—and learned a lot in the process.

I recently left my W-2 job to be more present for my two adopted kiddos and decided to focus on growing my portfolio. I’m now actively looking out of state. There are so many great markets out there, and if I could do it in my 20s with zero experience, you absolutely can too.

I've house hacked my SB home, currently manage both a short-term and long-term rental, and I’m putting in an offer on a duplex today. Good luck—you’ve got this! Living out of state doesn’t have to be a setback. There’s so much opportunity waiting.

Hi! New here. ;) I made an accidental post. I thought I was filling out information. Is there any way to remove the post?