@Orane JacobsWhen thinking about venturing into a new market for house hacking using a VA Loan, it's important to look at various factors like the cost of housing, how much demand there is for rentals, the job market, economic conditions, how fast the population is growing, what amenities are available, and the resources for managing properties.

If you are local self managing is not that difficult, you just have to have the mind for creating and following a process.

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

PLEASE get a property manager.

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

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.

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. 

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.