As such, we took the gamble we won't have a catastrophic loss from a NS and, if there is any damage, the same $10K we'd have to pay anyway with insurance will take us a good way to being "whole".My own personal home, which is a duplex, is insured at a $250K value and I pay $3600/year for that. 

I started going there since about 1990 from SoCal for fun and vacations so i've watched it evolve over the years from a dusty gambling town to an international resort destination and I see huge opportunity there over the next decade - it reminds me of LA around the Sunset Strip and Hollywood in the 80s when it was run down before billions of dollars started flowing in and now those areas are some of the most expensive in the city. 

I think it would be best for me to buy a home at a great price and make cash flow rather than gamble on what if's and buy a higher price home and not realizing any cash flow after I just bought it.

I have a strong desire to own more real estate but currently in Las Vegas the ROI isn't there unless you want to gamble on appreciation and I do not. 

(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.

You have a higher chance of getting spammed with the "hottest real estate opportunities" both on BP and on your email. 

Keep an eye on that inbox & possibly the spam folder. 

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.

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