So, you'll be subject to those rules and probably couldn't take them directly onto your 1040...I know businesses can have startup costs which I thought were amortized over the business somehow. 

A rough rule (very rough?) 

Easy answer is yes, must be in the same condition as they moved in, deducting any repairs needed from their deposit.

But a lot of the time the surrounding houses have been sold quite some time ago, and they are incomparable when trying to use appraisal rules. 

Estimated Rent (based on neighborhood median) = $2800Total expenses including HOA, Capex, Property Mgmt, and 50% rule for maintenance = $2750Cash flow = $50  :(Do I hold onto this gem or sell it and move onto a new strategy??

Financing is not easy to come by for tiny homes and RV parks and your cash out options down the road will be very limited. 

First off, while grabbing a lease agreement off Google might seem like the easy route, it's kinda like using a one-size-fits-all shirt for a diverse group of people; it might not fit perfectly.

You need to check with the PM company to see what they allow.I'd not do this because:You have to wait your turn for a booking.You  are at their mercy as far as rules and fees.Regime fees and special assessments can kill your net income.A SF beach house will make more money without the HOA fees.Condos are a dime a dozen in Myrtle Beach so you can rent one cheap due to all the competition. 

Historic appreciation across the U.S. is in the 4% and if you believe the 1% and 50% rules, you would get 6% return from rents. 

Fannie/Freddie money = Fannie/Freddie rules.