My (very) wealthy sister and banker husband bought and sold several houses during their economic ascension. His theory was this - always buy the crappiest house in the neighborhood. Then fix it up while you are there. When you sell, you get the best value back. Also, by buying the crappiest house in the neighborhood, you end up in the best neighborhood you can afford.
I do a lot of real estate work and I've moved enough to have purchased four houses for myself.
General thoughts:
Neighborhood/school is most important if you have kids. Care less about how pretty your kitchen is or what needs a remodel and care more about who the neighbors are and how good the school is.
Commute to work/school is important, but for me - and it's personal - I'd spend 10 extra minutes in the car each day for a significantly better place. I don't really mind car time, however.
Realtors, with few exceptions, work for the deal, not the client (save your breath BY realtors - I'm impervious to your mind tricks). Remember that. You have to be your own best advocate, for all aspects of the deal, from offer price, to down payment, to negotiations. When I sold a place in DC in 05, my Realtor wanted to start at a price 80k below my price. I insisted on my price. Got two full price offers on the 1st day on the market.
That written, a realtor doesn't cost you anything as the buyer - use them to unlock doors at your whim. Any contract you sign with a realtor you should keep to a minimum duration. Very easy to find another if need be if the 1st doesn't want to re-up.
Use your own independent inspector. They are out there. If you use the one that your Buyer's realtor suggests, you will likely be getting a rubber-stamper that will flag a few minor issues but will not flag anything substantial, because as soon as he gets the reputation as a deal-killer, he gets no more calls.
Put as little down as possible. If the real estate market is hot, you may have to put down more "good faith" money. In reality, standard Realtor contracts are garbage, and easily gotten out of by either side, so there is not much risk, as long as you follow the timelines in the contract for getting out.
Be careful of "liquidated damages" provisions in the contract. Feel free to send me a contract BEFORE you sign - I'll review it for free. That goes for any BY regulars buying a house (except for CL - for him, mostly free).
Keep us updated and good luck.
BTW - lived in Newington and Simsbury. Newington was nice. Down to earth, decent school, regular folk. Good location. Bit cramped. Simsbury was richer, idyllic, good school, with rich kid problems. Bit out of the way. Lived in Newington in the late 90s and in Simsbury in the mid 2000s, so not really current.
Good luck.