The responsibility of enforcing a lien is squarely on the shoulders of a lender. 

Yes, I know I can't take all the deductions that I could have if I owned it outside of my IRA, but at the time, I didn't want to pay the penalties and huge taxes to take the money out and I didn't want the aggravation of a lender looking over my shoulder and demanding that I hire certain contractors to do the repair/remodel work.

Don't try to take this burden on your shoulders.

Also if possible, have a parent signature on the lease and they may shoulder some of the responsibility... hopefully 

Your dues lend your shoulder to the legal battle fighting the insanity.

The penalty could have been upwards of 350k though and that wasn't a risk we were willing to shoulder.

They don't need a babysitter checking over their shoulder every three months.I inspect once a year, typically in the latter half.

That being said, VRBO still rules the summer (7 day minimum weekly guests) and Airbnb dominates the shoulders.

The shoulder season is always quiet, but you could likely get 30+ day rentals in the summer.  

However, that came at the cost of starting with little to no equity in the property and shouldering a more substantial monthly payment.