How have you done with expenses, quality of tenants, turnover, cash flow, their property management team, customer service, etc.  

I have a client that is asking me to manage a short term rental for them and i wanted to get some insight from anyone thats managing an STR currently as I have no experience in this field.

From the property management perspective, yes...hot tubs (actually in-ground spas) can be a pain.

Big banks and banks in general often do offer great terms for jumbo loans, especially if you are willing to bring your assets over under their management. 

We will hire a property manager so that will be 20% commission.

I would prefer a brand new or newer home as I would be managing it from Miami and rather not use a management company. 

In this instance, just go address it And in the future, don't let this happen.For your vacation rentals, make sure there's a system in place where when any service is done there's photo proof, a timestamp, property manager digitally acknowledges, and a physical receipt there.

I sold a condo here, really wanted to keep it but HOA was badly managed, 4 increases to HOA fee in 2.5 years.

I have a friend who has some real estate experience (mainly legal, local knowledge) that could be 'boots on the ground' in terms of understanding the locale, assisting with property management.  

Means they are below what they set in their management software.