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. 

Even if it takes longer to pay off, having a steady, reliable tenant might actually be less stressful than managing an STR.FYI - consider starting with a regular rental but structuring it as a 6-12 month lease.

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

It may effect lease renewals.  

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

And don’t be afraid to chat with leasing agents in Brickell-they can give you a boots-on-the-ground perspective on rental demand.Natalie, your story reminds me of a friend of mine, Alex, who house-hacked a two-bedroom condo in Phoenix.

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

Get to work on it and lease it.

Without getting too deep into the weeds, there are a few ways to do this, including:- write up an assignable lease and an option to buy which the seller signs, then assign the lease and option agreements to a tenant-buyer.