Below are some of the data points I'm looking at in each city, what would you add/subtract, or roast me for? 

I would check with the city of Littleton before I did much more.

Air Conditioning, if an city is hit or miss with A/C units does this play a large factor on rent and/or property values?

Both you and your wife should take the time to schedule a session together with an asset protection attorney who knows Connecticut and New York law.Good Luck!

First step is to check with the city or county to find out what the zoning is and the allowable uses are and what is required for development in terms of lot coverage, setbacks, height restrictions, utilities, access easement, parking,  etc.

Reading city for example holds the highest transfer tax in Pa, 5%.

In the city, there is a plethora of old multi-family properties that need to be renovated at all different price points2. 

But avoiding buying in cities in deserts or relatively impoverished coastal towns might be a good idea. 

Ideally I wouldnt want to live in a hugely rural area, but dont need to be in a big city either.

Quote from @Shrikant Kakani: I'm not sure how you landed on those particular cities.