And if you are not willing to make the 2+ hour drive  to invest in yourself, why should others be willing to do the same (drive from say Albany or Springfield) to invest in you? 

Hello everyone,My name is Eddy and I'm from Springfield, MA.

We invest, manage and buy/sell in the Hartford County and Springfield MA area.

About 2 weeks ago, I closed on my first investment property, a 4 unit in Springfield.

Our friends chose Springfield because it was even cheaper and you got more home for your dollar.Good luck!

We are thinking of looking in another city such as Springfield, MA we are not sure of the market over there and wanted to know what other investors in the area think and feel about the current market.

I'm just about 20 minutes from there in Springfield.

Clarksville, Shelbyville, Columbia, Springfield all have opportunities like that. 

If you expand your search to Dayton/Springfield/zainsville you might find better properties but the appreciation/tenant pool would most likely be significantly lower than in the three major city’s you referenced.

If you've  ever driven through Springfield Wisconsin and saw the 1870's brick Church , I converted that into a house for my Sister - it was featured in the Milwaukee Journal.