I had analysis paralysis yes it’s a real thing, even if it’s just an umbrella term for a multitude of factors.

I find the whole situation frustrating AND hilarious.

Can usually allot 5-10% vacancy factor and same for maintenance.9) Class B usually also okay, but needs more attention from owner and/or PMC.

Be mindful when you do the cost segregation study, the basis will be based on the carryover basis factoring in the deferred gain via 1031 exchange.

Loan amount, fico score, experience and occupancy play a factor. 

You also mentioned that it's an STR with an average stay of less than 7 days, but that's not a factor on whether it goes on Schedule C.But just so you're aware, providing hotel-like services so you can put it on Schedule C isn't the only way your rental losses can offset your other Schedule C businesses and your husband's W-2. 

Are there any key factors to look for in selecting a good commercial property real estate agent?

Here is the summary if you are interested.In this case, the main question is when did the investor completed his start-up phase and became actively engaged in his business.Whether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business: (1) whether the taxpayer undertook the activity intending to earn a profit; (2) whether the taxpayer is regularly and actively involved in the activity; and (3) whether the taxpayer's activity has actually commenced.

Done properly, an investment made today should have “priced in” the factors the were previously unexpected and resulted in trouble. 

Also factor in your capital, time, energy, skills, and other resources.