I've spent the last 3 years nagging the city to sell me a lot next to my property so I can install a driveway and they've finally agreed.

Plan would be to sell. 1.

After two years, they can sell the property to you as your first solo investment.

From google: “The Fair Housing Act (FHA) does not apply to certain types of rentals, including: Owner-occupied buildings: If the building has four or fewer units and is owned by the person who lives there Single-family homes: If the owner rents or sells the home without using a real estate agent, and they own no more than three homes Religious organizations: If the property is only available to members of the organization's religion Private clubs: If the property is only available to members of the club Senior housing: If the property is designated for people who are at least 55 years old Even if a property is exempt from the FHA, it must still comply with the law's ban on discriminatory statements, notices, or advertising.

I have been listening to the Rent to Retirement podcast recently and they have been heavily selling properties in Akron, OH and I have read some really good reviews about their experience.

We lived in the property for 2 years and rented for 2 years to tenants, so by selling now, we ensured that we could avoid capital gains taxes.

Seems like the exit plan is to sell to people who are also doing STR?

We've got tons of Churches in the ghetto where the pastor calls me trying to sell the building to me for 20x what it's worth. 

My grandmother wants to sell her home but live there rent free for the rest of her life.

If I sell this house today, I can get $460K but I still have mortagage to be pay off which is about $350K.