They do have a property management function that maybe could assist with this?

I would advise finding an investor friendly realtor when you choose a market.

House-hacking in a multi-family unit is one strategy I wish I had been aware of when I chose to purchase my first property.

The issue is the use of capital to buy a multi family for all cash only to receive a cap rate of 5.3%.  

Weekends for a lot of people are usually tied up with kids sports, family functions and trips.

You’re going to have to find a specialized function that can’t be farmed out to the Philippines in the $5-$10/hr range.

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

This will allow you to put the loan into the entity or business name of your choosing.

The last 12-18 months have been a little rocky in the DSCR space for 5+ units. I find DSCR most lenders are 8 to even 9% for max leverage on 5+ right now. I know of a lender around 7.3%, but curious what everyone else...

I’m actively analyzing the demographics and rental trends in the area to ensure these upgrades aren’t just attractive but also functional and desirable.