The better areas of Chicago just like the better real estate markets of the nation have quickly bounced back towards peak prices, so the equity bet is risky.  

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.