Your best bet is to crash on someone's couch until you have a job then start hunting for your own place.

Generally your safest bet would be to simply pay off the HOA to protect yourself. 

I'll bet you know a good lawn service who would work with you and do it for free or greatly reduced in exchange for the chance to get a long term client.  

I bet there's a house already for sale in the same area as your theoretical acreage, for $60k.

If there are, I can sure bet that the premiums will be sky-high, in that there will most definitely be claims made when they vacate.Your thoughts?

Some things just can't be answered in forums, so don't bet on getting answers to rely on.

@Irma Hermida To get your company builder credit and to have some kind of project registration/experience for future use, you might want to partner with someone and give/sell a portion of the land for them to develop and they cover the payment --there are investors that invest on appreciation based only--, but perhaps JV with someone is probably a good bet.

Mike,Comfort Masters is a great bet for the North end of the Eastern Shore (Cecil and Kent County). 

But if you aren't, it's risky to bet on appreciation in order to make a property pay off for you. 

I bet they will end up selling for another 30K drop though.