PLEASE get a property manager.

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. 

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

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.

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.  

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. 

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.