Great and intelligent conversation all around. I understand all perspectives.
The general CT market is going in the wrong direction, however, there are some bright spots. Personally, knowing the market and having good contacts is very important - and as @Victor N. said you must buy right here as I would not count on natural appreciation making your deal a home run. It's certainly possible that CT continues to have a downward trend and cities become very rundown, but I am cautiously optimistic that we won't go down that bad a path. We might not have the growth of other markets, but I think CT will be able to find a way to hold their own.
However, I don't think investing out-of-state [today] is going to offer lots of low-hanging fruit and a way to find easy returns, a lot of the upside in growing markets is already priced into the deal, so I don't think you're going to find smoking deals somewhere else (unless you have a particular insight to a deal or market). And a state like Florida - which is an amazing and growing state - is also a more finicky state since some of the bigger industries are related to tourism and foreign buyers, which is tied directly into the economy (which is one of the reasons it was hit so hard during the last downcycle). It's very possible that it will be more insulated now than it was in 2008 and it can sustain another recession better than the last one - due to more businesses moving there and a bigger population - but I don't think it's as recession proof and a chance prices and rents have some sort of correction.
Ultimately, I think the people that will do best acquiring in this part of the cycle are the people that identified unique opportunities that someone unfamiliar with their market would be able to determine. For example, under market rents; a driver to a particular town; etc.
