Doing so will likely eliminate all extra cash for several years, keeping me from investing.

Even with the extra village tax, I like the walkability and village feel.

If you are comfortable with a property a plane ride away then your predicament is just a math problem to determine where your money/ equity earns a better return. 

Set aside extra contingency money to cover the unforeseen2.

However, I still expect average occupancy rate of 80 - 90% is very much possible.On average as an investor, I would expect to earn between 8 - 12% ROI, if you are doing everything right.All the best!

Wanted to reach out to the Central Florida BP community and see if anyone could use an extra set of hands on one of their rehab projects.

If you have a closet that's all you need and you should definitely close the wall off so it could actually be used as a bedroom.  10'x10' is very common bedroom size in Chicago, although its not ideal it can easily fit a full soze bed with extra room.  

The next door neighbors (it's a multi-family unit) are also very nosy and in close proximity.The comp down the street sold at around what we are asking, but it took 90 days or so.I calculated the cost of money, utilities, taxes, etc, plus the loss of potential earnings on not recouping the money, at around $4K a month.

Once you are in a position to move on to the next property, rent out the unit you are vacating and hold on to it for extra income.And do yourself a favor, use a VA guru lender that knows their stuff, not the call centers (USAA, NFCU, and VU. 

The end game is what's in question here.I'm thinking we take a flat cut off our earnings, but the majority goes back into the business