@Dallas Smith To defer capital gains on your investment property, a 1031 exchange is an effective strategy, but the replacement property must be held for investment purposes for at least two years.

I realize I am not cut out for the entire REI process of consistently finding multiple properties for particular exit strategies. 

You can only sell it to landlords using the rent by room strategy.

Most ideal would be seller financing, but open to creative strategies for a cash-flowing property. 

Solid strategy!

Anyone that is looking at your assets is always going to need to factor in property management, so you can show that as a real expense (and really make it as high or low as you want).I work in a vertically integrated real estate and development company, and I cannot imagine how things would run if we did not have an internal property management company that essentially works for the other companies but also stands on its own.

Dou your work on the education so that you can have a firm strategy to get started.  

Additionally, they have another property which has appreciated in value, carries low interest rates, but has negative cashflow and essentially feels like it just locks money away.

This means you essentially have to save buyers 3x(5k-10k) = $15k to $30k through negotiating, finding the best deals, adding value with your property management or contractor contacts, etc.Lawyers use flat fee, hourly, and contingency pay structures primarily. 

I think you should seriously consider your financial goals and strategies.