I am currently 24 years old.Here’s a little information on my current property (primary residence):Purchase Price: $130,000.00 Mortgage Balance: $99,937.34 Market Value: $180,000.00Market Location: Spring Hill, Florida, USA (Tampa Bay Area)Of course, the best scenario would probably be to move back with my parents, but, truthfully, I do not want to move back with my parents and siblings; however, I would be debt free and generating income from my primary employment.I feel that the downsides to selling my home is that the market in my area (currently a seller’s market) is extremely hot and, by holding onto the property, there is a likelihood that the value of the property will eventually increase substantially over the next few years.If you were in my position, what would you do?

I’m in a similar position as you.

The more familiar you are with the area you buy in, it puts you in a better position to know pricing, neighborhoods, historic trends etc.

Unless there is a typo my guess would be that you are possiby entering the amounts in and out backwards - using negative and positive numbers in reverse.Another common mistake is the timing of the  money in and out.

It is a 2 bed 1 bath + office apartment in an old but well maintained building.

You could try to get your unit rented or get another unit that has a positive cash flow that you desire. 

There is a reason why you maintain property insurance.

Just some made up numbers for an example:Original mortgage payment: $1000 monthHELOC payment: $500monthTotal:$1500Now rental #1 cash flow $400 positive per monthRental #2 cash flow $400 positive per month=$800 - $500 = $300 more in your pocket per month than before.

I'm curious as to the contracts with the city, in terms of length and the likelihood of the city pulling out of the program (assuming everything with the agreements is in compliance and maintained).  

I personally prefer a legal position involving deeded ownership or secured lien position; however almost any real estate activity can be profitable given the right set of circumstances.