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.

If rates stay low and we continue to have zoning/permitting regulations that aren't conducive to building more units quickly, demand will be high and supply will remain low which will lead to further appreciation. i saw a recent study that said sellers prefer offers using conventional financing as opposed to FHA because FHA takes longer to close and has more strict inspection requirements.

Any preferred methods or ideas would be a huge help!

BTW, BECAUSE we tell our sellers we have zero interest in buying their house( when we think that deal is a better fit for wholsaling  as we usually flip) they prefer us to wholesale rather than buy it ourselves.As you can see, the only challenge when it comes to wholesaling is, getting leads.