But when looking at the very low total dollar amount of actual profit and the very low cash on cash return, plus the time invested and stress of dealing with the repairs and bad tenants, and the risk of being in a market where a duplex only costs $200k which that location was the source of your problems to begin with...

So if the average tenant pays every month, nothing breaks and they all stay a year. 10 out of 12 months you’ll be missing 1 rent and have turnover costs.

Those "small bits of upkeep" seem fairly significant.

Also how much of a reduction do they want? 

It is complex but Airbnb seems much more on top of it than VRBO.

For now I'm doing tons of research, and getting my finances and DTI in line.

It's tricky and changes the dynamics of the relationship. 

the median age of first home purchase in the US is 38 so if you can do it by 28 you are way, way ahead of the game. 

Purchasing the LLC gives you ownership of the property, but it also opens you up to additional legal exposure since the entity has been active, and there is no way to really know for sure what else they used the LLC for.

They provide a decent amount of stability & return.