@Justin Cloyd,
Congrats on starting the investment journey! It seems that you have a lot of options at least.
1) Does anyone have any legal advice for managing a long term rental single family house in Portland? (Attorney and PM contacts would also help.) I know it's a very tenant friendly city, so I'm worried about the legal side of things and I want to get everything set up the right way.
If you are going this route, find yourself a good property manager. Usually, you only get to the attorney part if you have a troublesome tenant. I'd check out rarebird (they are a local and have A LOT of experience). You can contact Eric Guess there. Doug Moe with 24/7 properties is also great as well. They can direct you to attornies if it gets to the point of needing to evict someone. If you are going the self-manage route, I'd take a look at the local landlord association. They have classes and forms you can buy. Here is a link to them - https://www.portlandarearoa.co...
2) Getting the right terms on the home equity loan is the key to keeping it as a rental from a cash flow standpoint, keeping the favorable existing 3.75% mortgage intact. Any recommended investor friendly Portland lenders out there that I should talk to?
At this point I would look more at HELOCs (they are different than home equity loans). You will currently not be able to find a great cash-out refi that makes sense with an interest rate. You might be able to do the cashout refi and buy down the rate significantly, but I don't think you can buy it down that much. Contact Cori Angel at Bank of England (DM Me if you want her contact info or Google it) and you might be able to talk to her about getting creative.
3) The alternative to renting out this house is that I could take about $100k from the sale and invest it elsewhere. I'm comfortable with new development, or in Ohio rental markets (Columbus, Cincy, Dayton metro areas). Obviously understanding these investment alternatives would be on a case-by-case basis but my gut says the low interest rate on the existing mortgage makes the existing house the most fruitful deal since the Portland market has been appreciating faster than Ohio markets for the past 20 years. Development might also make sense if construction and land prices pull back a bit. What are other people's thoughts on this option?
I called about 8-10 of the local banks and bigger ones and found Keybank has the best HELOC program and OnPoint is the second best from the research I did. DM if you want me to send you some good contacts for the HELOCs. This would help get you the 100k you are looking for.
Development would be an interesting prospect. It would consume a lot of time and take a builder who can help you realize that. We are still way under the amount of homes to meet demand right now. This would be a large time suck though and if you are looking to build in Portland it will be a permitting nightmare.
Ultimately it boils down to what do you want to do in the future? What type of investments do you want? If you want to do something that will lower maintenance and you oversee I'd look at going out of state. If you want to do a bit more work and stay local, I'd look at Salem or something a bit further outside of Portland to reinvest.
If you want to have fun theorizing and talking let me know! I'm a big fan of architecture and would love to understand building multifamily apartments. DM if you want to set something up or you can set up a time using this link if it is easier https://calendly.com/agentlivi...