@Shaun Geary I just saw a list the other day that showed Vermont as the #1 tenant friendly state. You can't charge late fees, you have to give a 14 day notice to vacate for non payment, 60 day notice to raise rents. you have to hold all possessions left behind by a tenant for 60 days. Evictions can drag on for months and months.
That being said, all of these things only hurt you when you get a bad tenant. So if you do your due diligence in screening and place a good tenant the "tenant friendly" stuff won't hurt you. I've been a landlord in Vermont for 2+ years now and I've had no issues. Granted at some point I will get a bad tenant but i figure if I am screening very carefully it will be insignificant.
I also own rental property in New Hampshire and I will say what I like about Vermont is you can charge as much as you want for a security deposit whereas in New Hampshire you can only charge an amount equal to one months rent (regardless of if you call it a security deposit or last months rent), meaning you can charge First, Last and security.
As far as Buying property in Springfield, I live 45 minutes south in Brattleboro. I look at the MLS listings for multi-families in Springfield on occasion. The prices are attractive but I know Springfield is struggling economically and I'm thinking there is a good inventory at low prices because they can't keep them rented. Checkout Springfield Craigslist apartment listings, It looks like those listings stay up for a very long time, not like in Brattleboro where I can have an apartment rented in 3 days to a qualified tenant.