We have operated STRs since 1999 and they had been around long before then (STEs have existed for many decades).  

In the spirit of order of operations, might be helpful to break down in this fashion: 1) With your 401(k), do you have pre-tax money and post-tax Roth funds?

Has anyone been in a situation where they acquired a condo and operated it as an STR when the HOA did not make the exclusion in their CC&Rs, but then faced resistance from the HOA?

I have an operate account for my cabin that I pay for as a backup.

Operator positions themselves as the owner of the Property Management company when they in fact, are not.

Having someone who has owned and operated a similar asset is worth its weight in gold. 

@Kayla Givens Do you own the houses where you operate the SL homes?

This is definitely making me rethink if it's a worthwhile gamble (especially considering the owner that is bey foreclosed on is supposedly a lawyer).

Yes, you can ultimately own a property with little/nothing out of pocket when you're done - but when you reposition with today's rates even moderately leveraged stabilized assets can be hard to find cashflow with debt service and a realistic operating expense load.

We had to 'pierce the veil' and have an underlying partnership agreement, bank account in the partnership name rather than Land Trust name, but it did work out to open an operating account for each property.