It's just gentrification process from baby boomers/old timer settler to the new tech generation. 

I’ve done my best to research the process but wanted to get additional guidance.

Now these check writers are unfortunately being targeted by individuals with bad intentions. 

@Joel HuntYup, so as you've surmised, your borrower processed the 1099 incorrectly. 

In process of looking for new umbrella myself.  

Are there any guidelines for situations like this where the tenants would need to stay somewhere else while the renovation is in process?

Thus the whole process costing you a few thousand more.  

This individual has successfully been doing property management through a company that has supported him in addition to his off-line unrelated real estate duties that he successfully continues to manage.

A couple of months ago, I started the process on a HELOC and assembling a team in Sacramento to make this a reality. 

How many individual owners and how many are part of a group?