Are you willing to gamble the $2,500 that your going to find a buyer?

You really need to find yourselves an accountant and attorney with cross-border real-estate experience and find the organisational structure which best meets your needs.Where you will be five individuals, entering this venture, @Matthew Lee is correct about doing a level set with everyone, before monies are committed.  

Then it's the gamble of did you get a added 15, 20 or the coveted 30% off added coupon??????

It could appreciate but I consider that gambling.

Better yet look closer to MA border.

I think he will find more Spanish speaking people in the cities and closer to the Massachusetts border.

For example, the Hillsboro schools have for years been considered among the worst in the state (they're improving), and Hillsboro borders the Contoocook Valley and John Stark districts, which are excellent.NH also has few traditional neighborhoods in its smaller towns.  

I generally do business from Waterbury to Stoors (UCONN) from west to east, from the CT/MA border to New Haven on I-91 and the entire route 9 cooridor.What kind of deal is it? 

Personally I think buying in Dover is much more palatable as an owner occupied house hacking scenario, which won't work for you,  though enough of you guys move north of the border maybe you can be persuaded :).Rochester is often mentioned, and there are certainly good deals there.

So now, at this point, you are pretty much gambling on your flip if you use anything else except SW.