If 1099, why can't he get his own liabilty coverage?

He owns a 3 BD / 2 BA in Tacoma.

Most DSCR lenders actually prefer you to own the property in an LLC, although some do allow you to close in a personal name.

Personally I think both are important.

I personally couldnt return to lock the garage.

As noted above, having an agent that is familiar with investing can help in how the investing market looks versus how buying a personal property looks.

I am not able to take equity out of my condo because it is currently on the blacklist due to HOA fixing the roofing and a Fannie Mae rule stating, if more then 50% of the condos in that community are owned by investors, I may not be able to refi.

And personal downsizing is always good for business!

And you now own real estate that will hopefully appreciate and when you move out will potentially provide cash flow. 

I personally use Quickbooks online and have a virtual (remote/nonlocal) bookkeeper.