My long-term plan is to build a house (and a few additional structures) on one of those properties and eventually retire there.I would like to act as the owner-builder.

You'll end up in front of the right people eventually. 4) Keep going to those meet-ups and be a regular face there, not another "here one week and gone the next".

If you see yourself eventually helping other investors buy and sell, or want full control over how your own deals are marketed, then the license starts to make a lot more sense.

Interesting data - I still wonder where the western NC second home market is going to settle out from all of this.100%+ price increases since 2019, prices seem down a little from the 2023 peak, but it also looks like a seller's strike in the market I'm occasionally looking in.Not that many listings, still elevated prices, and properties either get pulled after 3-4 months or there's a grindy sales process and eventually someone buys for a little less than the previous comp.

So, eventually things are likely to change again. 

Or that they eventual payout would be deducted by the loss?

Hi @Lenny MarkusIt sounds like you are in a situation that many landlords eventually run into, and the key really is to protect the property while keeping things professional and organized.

@Mic Salvador,Great advice above, and definitely get a good team together of people you trust: a lender, real estate agent, contractor, and eventually a CPA, so that you can make the most of your investment.As some have mentioned, the market can be tough for new investors, so go in with a clear plan, and let that plan include taxes.

especially if you plan to leave and keep it as a rental you'll want to make sure the condo association does not forbid what you eventually plan to do with it, ie ltr, str, mtr etc. 

Eventually Seeing real estate as a resource rather than the finish line is a lesson a lot of people only learn the hard way.