If you are near the border it may be worth it to look into more but if you are not then you are pretty much stuck paying the premiums.The maps are updated as technologies, methods and data become better at predicting which areas are higher risk but that is out of your control.

If you are going for appreciation/gambling, then open any real estate article and they will tell you the highest appreciation that happened in the previous quarters.

This would be a gamble.

However, one thing is certain, if you are going to gamble, Las Vegas is ironically a good place to do it.

I currently have access to two single family homes (375-550K FMV) in Southern VT (one near the NH border) that have 50-100K in equity that I would be able to assign a contract to.

High rates of return are addictive and there is a fine line between investing and gambling.   

It can't/shouldn't - unless you have a partner you really trust or want to gamble. 

Lease 2 own exit is a gamble as an exit strategy too. 

I'm working on a parcel right now that has some old graves on it, is bordered on 3 sides by an old landfill, a sewage treatment plant, and a radioactive waste storage facility, and there are 2 homeless squatters who have been camping on it for 5 years. 2.)

This is like asking a casino-paid gambling consultant to help you beat the house - it's a conflict of interest as few buyers agents (who are also paid on commission) are truly motivated to negotiate themselves to a smaller sales commission.