(and anyone else following): you’re right that this is still a bit specific to the Boston market - generally for investors, sellers will assume a $1k waiver is just a gamble you’re willing to give away if you want to back out.

I am a computer geek by training, but I am interested in generating passive income so that my family can have financial security and the opportunity to travel and have adventures (without the day job). 

Some charge me yearly others are 3, 5 or 10 years but I can’t think of a scenario this would work me unless I inherited a $500k IRA or really wanted to manage all these accounts & fees & IRS contribution & withdrawal rules or I took on a large gamble investment for a 30 to 100% return & got into active market again like flipping houses, etc.I guess I would rather pay the IRS less than a company like Quest IRA?

I think what Lucas is saying is you’re gambling if your game plan is to have a short term rental in a community of primary residents.

I already see seasoned investors becoming cautious and less adventurous in their risk taking.

Welcome Ben, I am 35 and just now looking to get started in my real estate adventure! 

So basically I'm gambling on appreciation, with crappy tenants, asbestos, etc. 

Good luck on your adventures! 

Or, am I just gambling with the appraisal fee and hoping for the best? 

., an optometrist, a vagabonder and an adventure junky.