I do single family houses with minor to moderate rehab.

That area is growing but is a bit of a drive and still moderately expensive.

By the way, it says you are a Moderator.

Like any product, some will sell that product for an expensive price, some a moderate price, some a cheap price. 

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.

We were investing in real estate before the crash so we are moderately seasoned investors.

This is behavior unbecoming a moderator.

MODERATOR:  RECOMMENDATION ONLY, PLEASE. 

If he has been living in the house for 20+ years and is a moderate to heavy smoker, there may be rooms where scrubbing, sealing and painting simply won't keep the chemicals from coming to the surface and you will end-up pulling down the drywall and hanging new.We renovated a house some years ago where the former owner had a favourite chair in one corner of the living room where she sat and smoked.  

If you look at margins nationwide California,Parts of Florida,New York,etc. are all speculative.I remember a 4 or 5 years back in Miami there would be only so many condos being built and sold in a development.The investors would pay a homeless person (no joke) 100 bucks a day to stay in the line for them.They would buy up units and then immediately maybe in 1 to 2 months flip them for almost double.The markets were totally crazy then.Same stuff in Cali where brokers were telling me trailers were going for 750,000.So some of these investors that bought and made a ton along with foreign investors are ready to play the speculation game.They are not really in it for the cash flow.They already have a nice portfolio and chunks of cash to allocate funds to speculative investments and if they don't all margin out they will be fine.Speculating is fine if you have the money to lose and still be flush with cash.So these speculative markets have very wild swings in values.First to tank down hard and first usually to start going back up.In Georgia we have more moderate peaks and dips.So with some appreciation back but not huge swings in the future you need the cash flow as part of the deal.I don't like speculation just the hard numbers.I will speculate to a degree on land for future commercial development but I won't buy a house that loses money every month just on the potential of appreciation in the future.