I have a tenant who can be erratic & make poor decisions that have effected my condo community and pissed off the HOA, neighbors & me to no end, so I've chosen not to renew his lease. 

I am a newbie starting out and I have chosen to go the wholesale route.

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. 

Thus the functionality of following your chosen individuals and making extensive use of setting up keyword alerts with words or terms such as course, workshop, event, coaching, mentorship, analysis tools, multifamily real estate syndicator and the like.

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.

Curious what your chosen market is?

Does your chosen major directly translate into money/job you like?