A lot of this content was produced in the mid stages of a vacation rental frenzy, and those concepts don’t necessarily work any more.

Working with the city to find a solution.There is a similar situation near me where an investor bought a short term rental house, rehabbed it, ran it for a while, and then got in trouble with the town after a neighbor complained and the town said short term rentals weren't allowed in the community. 

LMK if you have any trouble there.

If you don't feel it's worth the trouble then you may choose to move on from it. 

Stop using the cash money as those are only going to get you deeper in trouble with their fees and interest rates. 

I house hacked both the properties I have and thought I should put them into LLCs for liability purposes, did not realize that I would have trouble getting a HELOC in the future.

It's not as simple as simple as buy now and hope that "time in the market" will produce a win for you.

Some syndicators have so many fees (acquisition, construction management, asset management, capital event, disposition) the syndicator is going to get rich even if the deal produces zero return for its investors.

Some of our deals produce out size returns, but most are in the mid teens.  

The insurance agency I work with is having trouble finding a company that understands that type of policy and also offers it.