I cant decide if I want to hire a property management team to rent it out for me or if I want to hire a real estate agent to sell it on a rent to own basis $1000 down $250 per month over 5 years.Is it smart to have BOTH options on the table at the same time and whatever happens first go that route?

Recognize that your partner is bringing the means to the table. 

Next thing you know on your next deal, your seller will look across the table and tell you "I heard what you did for so-and-so and we've been friends for thirty years..."

Bridgeport is unique due to its geographic location and low barrier of entry for multi investments.

She finally vacated on day 21 and the per diem used up the entire hold-back, meaning that my buyer was able to keep it.What I found astonishing was that she showed up to the closing table without the slightest idea of where she would live next.  

missed one over a smoke detector that tenant had taken down and set on side-table... it was literally within eye-shot...

I do not spread 50 application form on a table or counter. 

AL has unique laws, supposedly you get reimbursed for the “value” of the improvements.

If you lived in it for 1 year and have to move for job related reasons you'll still get 50% of the gain up to those $250/$500K limits.Take the money off the table and look to your next acquisition close to where you're going to reside as you get to know that market.

No, this is not an unusual or unique opportunity, you just need to know what you're doing - like with any area of real estate investing - and you MUST know your real numbers.Good luck to you!