They should keep you compliant with all state and federal regulator rules and can ensure the loan is being created and underwritten to the proper guidelines.

2-4 unit properties usually have for flexible financing options as they fall under residential lending guidelines.  5 units is the smallest possible # of units for commercial.BP article with info here: https://www.biggerpockets.com/blog/single-family-small-multi-or-large-multi

Or is it more of a "yes but low llikelihood" type of gamble?

Are you familiar with their underwriting guidelines?

All the time: people mismanage their finances, they neglect repairs, they gamble too much, they become hoarders.

I'm trying to figure out why this wouldn't be possible based on IRS rules and guidelines.

The old adage about not gambling with more than you are willing to lose certainly holds true here.

Stock market is an investment, and as such is still a gamble.

Pretty safe gamble looking at what Boulder has done in the past, but ultimately a gamble none the less.

@Tom Brickman Cashing out investment properties inst a daunting task if you are working with a loan officer who understands the ins and out of investment guidelines.