As I'm sure many of us experience, I come across numerous seller's who would like to sell, but their house is in good condition and want market value. 

The question I'm getting at is risk, and the relative security of your investment in unforseen economic conditions. 

Lucie4) Nashville5) Raleigh, N.C.6) North Point-Sarasota-Bradenton7) West Palm Beach-Boca Raton-Delray Beach8) Punta Gorda9) Spokane-Spokane Valley, Wash.10) Olympia-Tumwater, Wash.Florida boasts five of the top 10 markets with the strongest commercial markets – a ranking that includes the apartment, office, industrial, retail and hotel sectors – according to the National Association of Realtors® (NAR) Commercial Market Conditions Index rankings for the second quarter of 2021.To find out more, check out this article from the FL Realtors 

Rentals in similar condition in the area are getting as high as $1350/mo!

During ownership, the county assessment amount my have risen at a slower pace than market value, because of the tax statute, not market conditions.

He wants to keep most of my deposit, deducting for items that were in poor condition when I moved in and only returning 15% of the deposit to me.

Since you are saying that the property is in good condition, maybe you can do without the MC for a few years?  

Either a probation condition or an existing no contact order.   

@Dominick Galinis two major reasons, actually:1 - the best properties to BRRRR may not be eligible for conventional financing due to their condition.  

We STR owners need to stress to everyone - neighbors/City Govt/Etc that STRs are (almost) always in perfect condition.