I do have family in WI, but I am trying to avoid sharing their address with my tenants and I am not sure my family wants that either.Thanks!

Just to avoid PMI?

Avoid the large national banks (wells fargo, chase, us bank, etc.) as they are a waste of time and completely inept to understand the needs of local customers. 

The realtors in my market don’t know how to price anything so trying to avoid them.

You aren't getting 120k or 200k in this deal because one who would avoid all the reasonable questions back is one who is not nearly as close to this deal as they think.

I would absolutely chat with the city licensing dept before moving forward with your plan.If you want to skip STR and focus on 30-day plus rentals, you can avoid the licensing restrictions.

People wanted to avoid airplanes or hotels to avoid being around people.

Which companies would you recommend using or avoiding?

Looks like if we were to build up the berm higher (or some kind of retaining wall) and over a certain distance to where the property elevates we could avoid this in the future. 

You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.4.