It can't be any more difficult than your regular job. 

Is this event still taking place regularly? 

FHA is good too... but you end up paying some pretty hefty Mortgage Insurance Premiums (regular Mortgage Insurance for a conventional loan is generally lower). 

Vacation rental property managers are much more expensive than regular rental property managers. 

Many people would want to “reward” themselves lavishly and regularly for working like that.

There is a group of a dozen of my regular STR tenants coming here in a week. 

The requirement that you not personally guarantee any loans taken by your IRA/401k is a corollary of this rule.UBIT/UBTI/UDFI: Traditional IRAs/401(k)s are tax-deferred and Roth IRAs/401(k)s provide tax-free earnings - with regard to "regular" income tax.

The deal with the non-performing note is to purchase at a substancial discount and try to get it performing again so that you either have a performing note that pays regularly or sell it in a few years as a re-performing note(lots more than a non-performing).

@Grant Anderson No bank will give a regular conforming loan to an LLC.

If your regular depreciation is already more than covering your cash flow, you will likely see little to zero benefit.