I know STR's that don't have pools don't perform nearly as well as one that does so factor that into your rental comps. 

Your PM will affect all aspects of your asset's performance and shouldn't be an afterthought! 

Unless your refi rate is substantially lower than what you have now, a refi will only drive that performance lower. 

My question is whether it would be possible to get an investment/asset loan (based on the property income/performance not my own credit/income) itself under an LLC and rent it to myself.

Rent--perform some basic rehab to get it rent ready and then rent it out; 2.

You can bet on your tenants being in place over the next year and that cash flow coming in over that 1 year lease, but you can't be sure how the stock market is going to perform over that same time period. 

Here is generally how the strategy plays out: when a sponsor acquires a property, performs a cost segregation study, and takes the bonus election, the portion of the property's value that is allocated to land improvements gets depreciated 100% in the same calendar year the property was purchased.

If said rock-star can't perform, is an extension at all possible?

When I try to look at new markets, I like to look at the listings right on Airbnb first, look at if the current BNB's are performing well?.

When setting goals I've found that a goal that you can just barely make by stretching just a little bit is the best.