Hi Alec,
You are asking the right questions. The simplest way to analyze STRs is by comparing revenue to the acquisition price. After you have a basic understanding of a given market then you can start debating the details.
For instance, my team purchases and manages STRs in Maui. All of the condos have HOAs (with high fees) so that wasn't up for debate. That market, however, has year-round seasonality so we get steady cash flow with little vacancy.
Deciding on STRs is going to be very subjective but it'll come down to what properties have the greatest yield. We have condos we paid a premium for to get direct oceanfront views and others across the street from the beach with no views. All of them are returning what we expected, relative to our purchase price. The views help marketing but if the property costs double for a view and only generate 20% more in revenue then you may have to rethink.
With all that being said, the short-term rental space is promoting unique listings. Try to find a property that enables you to stand out from the competition.