It does later say in the agreement that it is:"binding upon persons who own, lease, sublease, or occupy any parcel or portion thereof"The inclusion of which seems to imply that long term renting and/or subleasing would NOT be commercial use.I'm trying to figure out if I'm taking a significant risk buying this property for use as an STR.

If your cleaners do the laundry at the property, get the biggest one you can.Our cleaners do this at one property.

Lease is coming up for tenant and we would love to sell the property, but just don't think we will be able to get what we payed for it back in the summer of 2018. 

Typically in commercial leases there is a non-compete clause.

A lot of this process depends on your laws regarding STR and Mid term leases/occupancy?

I’m not able to personally qualify for cash out refinances.I’m looking to sell my home located in Southwest Florida in a HOA community but want to remain in the home to lease- 3 years or more.Does anyone have experience with this type of program or have any suggestions for me on where to look to get this done.

Over the next 3 - 5 years I plan to 1031 exchange all of our single family homes and purchase another 40 that won’t have mortgages (we use the lease option model to sell our properties to maximize profits so we cycle through properties every 3-5 years).

It may effect lease renewals.  

Is anyone familiar with a private lender, buying a short sale in foreclosure and leasing it back to home owner with the option to buy back with in 3 years?

This should be written in the lease and discussed prior to occupancy.