Factor in what has to be done for the exterior as it relates to your desired exit date: Paint, mud-jacking, concrete pour, roof, landscape, etc.

I'm trying to narrow down the "HOT" areas in Palm Beach County that are most desirable to Cash Buyers.............

The general rule is one month's rent in some instances  where an applicant may have  less than desirable qualifications  the security deposit can be increased  to compensate for those  deficiencies .

Renting it will take about 8 years to repay the line of credit and gain what i would earn selling right now.Selling seems the obvious answer but I appreciate any feedback.

I earn a decent amount at my job (I am a corporate lawyer) but since the recession, permanent legal jobs have been hard to come by so I have been doing higher paying contract work--I've been at my last gig for 10 months but you usually change jobs every month. 

I'm nervous that the owner might balk at the fee I'm earning and I can't afford to sue him right now and he doesn't have anything for me to get but equity anyway.

The Tenant/Buyer shall have the right to make such repairs, maintenance, and improvements as Tenant/Buyer shall deem necessary proper or desirable.

Esp if it isn't in a highly desirable area and this is your first project. 

Can you live on the $400-500/mo you'd be cash-flowing, plus your teaching earnings? 

The job market is skewed so there are mostly low paying jobs (restaurants, stores etc) and high earning individuals (business owners) 2.