Buying a house 1500 miles away - need a plan

If you are set on living in the eastern part of the state, then so be it, but if not, don't rule out the western part of Massachusetts - its actually a whole lot more like vermont (rural) than the other part of the state. If you were going to be looking for a career, the eastern part of the state makes sense, but the wide open spaces of the western part of the state, if you like that type of thing. In fact, western mass maybe a lot more like the topsfield area was 30 years ago.
 
Just my 2 cents worth....
We had planned for 15 years on moving back north to where I grew up. Bought the house, had it all "locked and loaded" to move up there when I retired....When the time came to move, we realized that the idea of moving back north was more exciting then the reality was turnng out to be. Fortunately we (DW) found a great place not too far from where we currently lived, and we are happy as clams.
Now we just have to sell our place in Virginia.......
I strongly agree with the idea of renting - you get a much better feel for a place than you do when you're just visiting.
 
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