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.

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

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

Even if I only have 1 repair in 2 years, I will be ahead of the game. 

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).

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.

The work performed at the rent due would be 2 entirely separate things but I would not rent a place that needed work in the first place.

Best way to start looking into this is checking comps on Airbnb, look for 30 day min listings and see how they're priced, who's booking (by checking reviews), how the best performing MTRs are set up.Start ups costs are very similar to STRs.

Should you perform maintenance?