I bet this place ends up being $600+ in the red each month.

Any time within the first three years the owners of said property can redeem their property thru the probate judge’s office.

@Storm S. so the due on sale clause can be called upon at anytime ?

Obviously if you have to grade an area lower, your best bet is pull the stumps, but if you’re just trying to make clearing and level land, are you a fan of cutting low, then grinding or something the stumps?

Figuring you're closer to the Medway area perhaps the Worcester Black Diamond meet up would Worcester or @Enis Shehu's in Framingham would be your best bet. 

I don't want to quit my job anytime soon.. but I want to supplement my ability to retire earlier, rather than later.

It sounded like you had a bit more to play with so I thought the stretch to 5% might be the best bet.

Your best bet is to build a local network so you can seek out input once you find some perspective properties.

And one of the advantages of taking a self-pace online course was that I could take the final exams ANY TIME I WANTED TO, saving a load of time.

I don’t think anyone should try and predict the future on appreciation returns, so your best bet is to look at past #’s.