In my area, houses don't go under a million dollars, except for bungalows.
In my area <100k is doable and possibly maybe for BTC if Bitpay was used. If you want details let me know via PM but I am no where near NYC or Chicago.
One area that would work imo is Pittsburgh as housing there is still reasonable, I am within 150 miles of there also.
If thinking about Chicago more seriously, Michiana/South Bend would probably work out well with the high-speed rail line back and forth from Chicago (... though it's still Amtrak). South Bend, actually, may even work with NYC. Flights are so cheap, the property tax savings would mostly pay for flights, and I'd get the transit line to Chicago, too. Last I checked, property was pretty cheap there, but I haven't looked in over a year. Maybe I'm overemphasizing location, forgetting just how cheap it is to fly once a month (I looked it up a couple weeks ago, I believe - DTW to San Francisco and back was only something like $260). I suppose anywhere with a fairly trafficked airport would be perfectly fine, which'd open the search to just about any small city with some Italians in the US.
ETA: Yeah, prices there are still pretty low. A place like this would make a damn fine home: http://www.zillow.com/homedetails/1646-Wilber-St-South-Bend-IN-46628/77022833_zpid/ - from the low-res pictures, and assuming no water or foundation damage, it looks like $10-20k (depending on roof condition) and some sweat would turn it into a very comfortable place. Or something like this: http://www.zillow.com/homedetails/1509-Wilber-St-South-Bend-IN-46628/77022854_zpid/ siding probably ought to go sooner than later, but the problems appear to be more easy-ish cosmetic stuff. Cabinets, veneer/wallpaper (had that in house in Erie - I can't remember what was behind it, though), kitchen needs some work... shed looks like it could be in poor condition - but it's a shed, so...
ETA2: Thread's irrelevant now, then. Lockin'.