The group of 4 probably doesn't want to live that way as well but with 1.8x the monthly rent where they don't qualify together definingly won't qualify on their own so they really have no choice. 

I spoke to a financial advisor for the first time, and throughout our broad conversation, one of the main points he hit on was my need for either an LLC or an Umbrella Policy.

It is a very broad definition. 

And although the "interests of justice" seems like a broad phrase, and most evictions are in the interest of justice if you ask the landlord, this is actually a very narrow standard.

But the majority of our lenders only require that a vacation/2nd home must have some personal use, they do not define the amount of days. 

A broad answer would be to definitely refinance prior to moving out, but again...the exact factors can change what the best answer would be.  

Generally speaking there are 2 main types of loans for investors: “Conventional” and “Portfolio”Conventional - I'll define these as loans that come from Fannie Mae and Freddie Mac (if you recognize those names).

Depending on how the boundaries of the unit and the Limited common elements, etc. are defined in the Condo docs you may own the sheet rocking, fixtures, interior wiring & plumbing, cabinetry, etc. within the unit. 

I understand that there are many more factors at play here, however, I believe that realistic goals are important and I am looking to validate  this broad stroke aspiration by asking more experienced real estate investors to weight in on this hypothetical.I am deeply appreciative of any feedback you might be willing to share with me.  

If you want to have a lot of direct control over your investments and want to be in the know about the day to day operations then self-management can be a better fit.Painting with a broad brush here, you can expect PM services to range between 6-12% of the monthly rent amount, varying widely based on a number of factors.