I'd also look into property taxes and what is included with that $800 condo fee (that is really high though guessing it may include weekly cleaning). 

.: I haven't passed this past legal review so for what its worth: Part of my standard requirements for everyone include income is at least 3X rent, minimum credit score, say 640, Clean record and no evictions as well as deposit is paid in full at signing of lease and 1st month rent is paid in full prior to handing over the keys.

I do however think as things clean up systematically, cashflow will improve and the benefits of low capX exposure in near term and appreciation will work out.

To set the stage, I'm owner of a short-term rental property in the Poconos in PA and we use a property management company for bookings, maintenance/cleaning, guest management, etc.This past weekend we had a guest booking but when the guests arrived Friday evening the house had no running water, though it had been running fine earlier in the day when the Property manager (PM) was at the house to give a final check and leave the welcome packet.

Luckily this apartment just needed touch up a cleaning.

A clean, neutral-looking curb gives prospective homebuyers a chance to visualize their own additions/upgrades.

The last time I stayed in one, I was charged a large cleaning fee and then met with a list of what to clean prior to us leaving.

so... clean-out and demo? 

You'll likely want someone that can handle A to Z with marketing, pricing, cleaning, maintanence, decor, websites, reviews etc.

He does not want to deal with the headache of tenants cleaning or any thing to do with STR.