Happy to provide more details.

On the llc side I will rent the property that I purchased from myself, and provide myself some protection of my primary residence.

If I invested 100K today, they are currently providing anywhere from 60 to 72% passive tax deductions due to cost segregation, depreciation, etc. 

Apologies for assuming the worst, but the post feels more like a pitch or marketing content than a standard forum post looking for help or providing subject matter expertise. 

And the guests are able to stay in a better property than a typical hotel room can provide. 

Hey Drew, get yourself an engineer to provide you with a report on the current conditions and the repairs needed.

Not having the latter I find myself on a journey to build a portfolio not just for wealth's sake, but to move the proverbial needle on beautiful design and provide a more pleasant built environment for all!

If it's currently an STR they should be able to provide you with the p/l statement from prior years so you can see gross rents, operating expenses, average daily rates and occupancy levels.

great advice provided - what I will add to this is if you have smokers and its not allowed I would offer to allow them out of the lease with no penalty. 

So, your focus may need to pivot from high rental cash flow to little to no cash flow as a rental with an appreciation upside.I would recommend taking your $150K to $200K and securing a solid equity position in something that will cover its expenses and maybe provide a small cash flow, but then is poised to appreciate nicely over the course of the next several years.