I thought the whole exchange was odd since I told him from the beginning I wasn't even looking for funding at this time but he definitely wasn't legitimate. 

tend to believe everyone is motivated by money; people who are lifestyle motivated think everyone is motivated by the least amount of time expended; people who are risk adverse can’t believe other people are willing to “bet” on outcomes even when the odds are clearly in their favor. 80% of the time (IMO) people who make decisions we disagree with are not making stupid, ill informed decisions or being “tricked”; they just have motivation, needs and desires different that our own.  

consulting  a civil right attorney is probably your best bet.

If he doesn't do biz structure or contracts,  I bet he'll have referrals.  

If so,Have you considered renting and turning your current unit into a rental investment (enabling a 1031 exchange after 2 years of rental income) ?

You bet.

In exchange, the former homeowner lives in the home until their death rent-free.

The process you are referring to is what we call a consolidation exchange, where you would sell multiple properties to buy a  larger property.

However, there were also multiple instances when one or both of us felt dismissed or disrespected during our written and verbal exchanges with Ryan.

In that price point, you'll do well to look in Seminole Heights.Value add will always be your best bet for better ROI, but out of town buyers usually will want as close to turnkey as possible.A pool will add 30%+ to your ADR.