Any / all insight, experience with occupancy rates, etc. would be greatly appreciated. 

So, splurging on a pool table, hot tub, and a telescope to enjoy the views would yield significant returns.I'd love to hear your thoughts!

Then you can just go to the chat, and analyze the deal, it can even pull CMA and rental estimates, count in the repairs and get you cash-on-cash or cap rate or whatever metrics you need.

I did a cash out refi on my principal residence at a much lower rate and paid it off.Now I plan on using the equity for more purchases.What? 

Removing problem tenants and re-renting to new market rate and respectful tenants.

Rated Very Good.2.

The issue here is in order to increase rents at reasonable rates to cashflow well you need to not just do cosmetic changes they require you to do extensive plumbing and electrical to be able to increase the rents. 

I probably wouldnt trust it 100% with that though unless I input all of the data that I have from my analysis in terms of ARV, rental rates, rehab rates, etc. now that I type it out, that actually would be a good idea aha. 

First, developing your awareness of the STRs around you is key to knowing how much someone is charging at any given time, the market's occupancy rate, and how much revenue your competitors are driving in.

I don't even mind paying ridiculous interest rates as I understand this is a big ask.