It might help to connect with local property managers who handle STRs to get a sense of what types of properties perform best. 

Compared to pre-TCJA rules, there is no material change in the tax treatment of a building involved in a like-kind exchange, where a cost segregation study has been performed.

Buyer is aware that seller intends to perform an IRS Section 1031 tax-deferred exchange .

Typically in company's 401K plan, there's a large-cap index fund option that more or less tracks SP500's performance.

I think that overall, multi-unit buildings will be your best bet if you don't want to risk getting in trouble with condo associations. 

@Shane Petersen from my experience, your best bet is to find and insurance broker that sells SafeCo.

Hey BP Community!
I’m currently on the hunt for my first investment property in Colorado, and I wanted to share my experience and hear from anyone who's been navigating the same market. Initially, my goal was to secu...

The lease agreement has a clause that acknowledges that the property is part of an HOA and that tenant indemnifies the landlord from non-performance ("hold harmless" clause).

If its' long term appreciation (which I'm personally not a fan of betting on) you can look at it as, if you put a small 3.5% down payment using FHA or Fannie Mae, and your property appreciates on average at 3% a year.

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.