- What are some of the preferred mortgage loan or broker companies (with lowest rates and fees)?

In reality, prefer it that way - saves on lease up costs, vacancies, etc.Good Luck! 

My preferred exit is always a cash-out refinance.

Before these folks moved in, I was in their apartment for weeks - drilling and sawing – not a preferred experience for the other 3 tenants in the building, I am sure.

Location isn't too big of a deal for me but preferably somewhere along the east coast or midwest would be good.

I prefer leasing to a group of students all on the lease and not by the room so then all parties are responsible for the missed rent if a tenant leaves.

I would consider leveraging your VA loan to purchase a place in Hawaii that you could house hack for a few years while you feel out your options and preferences while building equity. 

Not sure how to figure out occupancy percentages or over night rates.Go on AIR and VRBO - I prefer VRBO as a vehicle....Find a property (s) that are really close to yours in size, BR/BA, amenities Etc...Start with this month, then next month, Etc.....look at holidays and special events.

My experience is that if you are direct with your tenants and likewise compassionate (be a little flexible in giving them the time they need to vacate is preferable to eviction) they will go without much fuss. 

We could create an entity if that's preferable.