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

PLEASE get a property manager.

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. 

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.

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

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.  

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.

Even armed with 7 years of experience and over 100 units owner or managed over that time, I still see value in and pay for pricing software. 

my wife's company has had no less than 2 webinars a week addressing this and how to manage it they had the Lawyer for the Oregon association give a one hour presentation.