While the potential increase is a gamble from zero to infinite, the security of not creating a lease no longer appealing to the company is guaranteed.

It's really a gamble which way pay model is best, per-plow vs contract. 

CON- It's a gamble & if your timeline for returns is short then it may not be worth the risk.

Has the neighborhood improved or is it a huge gamble still?   

For the past three years, I have had a positive rapport with my neighbors and never had any issues until they moved in.The smoke triggered my asthma and made my son cough uncontrollably.

Unless you just have loads of money to gamble with. 

I would gamble it all, spend it on more toys than I can afford, give away to ungrateful friends, and be happy forever....

I'd probably be gambling on appreciation, refi after a decrease in interest rates, or forced appreciation / rent increase via doing a rehab the first year. 

We’re thinking through a few different options:- Moving out of our current house and making it a long-term rental, knowing that we could get about $1K/month in cash flow-Purchasing a house in either northern WI, or a dream location like the mountains of MT/NC/TN/WY that we could fix up and live in for 12 months, eventually converting to a STR (we’d like to take a gamble and live somewhere adventurous before kids, but settle down long term here in WI).

But its definitely a gamble Ps also in RI.