@Austin SteedIf you can afford all the LLC's, the extra holding company is nice in case you get sued or audited. 

I know other then adding extra bedrooms, bathrooms, or increasing square footage what else do you do to increase value.From your experience do appraisers really care about when appraising your property?

This will give you some extra time.

They red-tagged us and we were forced to pay for plans to be drafted, approved, and several inspections before they permitted us - set us back several thousand dollars and an extra two months as a result - still, we were able to complete the project and still appraised for more than we spent.

They are not free but give you an extra layer of quality control and accountability.  

You can also pay extra to essentially turn it into a 15 year mortgage.Now on the bigger more important question.

However, I like to hike, backpack, and do occasional remote trips where there is no cell phone service for up to 5 days. 

Extra features are always a plus.

Would you hire a dedicated property manager or would it be smarter to pay the short term rental cleaners extra to do any small extra tasks needed?

Massive amounts of wealth generation is happening for homeowners.What would you do with an extra 90,000 this year?