For starters it can be more difficult to find comps as there are often less multi fam trading than SFR of the same size and count.

Professional trade journals such as Accountancy, Tax advisor and others. 

I have been rehabbing houses in Milwaukee for 15 years and I am on my jobs at least 2-3 times a week - even though we use the same trades and typically do the same work.

Your background in Wall Street trading and current work at a property tech startup give you a great foundation for this journey.Starting with a rental property in North Carolina is a smart move.

I've invested in stocks, traded options, and even a bit of crypto for years.

(Most notably, they've gotten REPS aggregation all mixed up in the past.)Based on the regs seems that:- 1245 ordinary income recapture applies to some forms of property that qualify as "real estate" for 1031 exchange purposes- 1245 recapture on such "real estate" overrides 1031 deferral such that 1245 depreciation is recaptured to the extent there's a trade down in 1245 property in the exchange@Heidi Kenefick There are many additional mitigating considerations worth discussing in conjunction a real estate tax accountant.    

I totally agree, so many properties there are new and beautiful that there needs to be *something* to really stand outYou make a really good point re: no plan B, and in general I’ve seen the home values in that market depreciating (assuming because of the boom / growth in supply in the last couple years).I might be wrong here but I assumed that a general trade off between vacation market and metro areas would generally be that strs in vacation markets don’t really have a plan BI’m pretty split at the moment, but really appreciate your thoughts

I just read 5 books (out of print, published between 1979 and 1986) all related to wealth building thru real estate “trading and exchanging” (not for tax free exchange).These were the most convoluted, confusing, and unfocused real estate books I ever read!

Go to college (or, alternatively, learn a good trade) and set yourself up for maximum earning potential in a field that's interesting to you. 3.

I'm a member of GaREIA, they have a google group where experienced local inveztors trade tested (and mostly reliable) contractors, legal helps, strategy.