There are only a few providers willing to offer stand alone (meaning they do not also insure your properties) that have a minimum premium of under $1000 on properties deeded in an LLC, Trust, etc.For those investing in a single state, have less than 10 SFR, or if you can use the same provider that are insuring the rentals, that's when you can get an Umbrella for $150-$300 per $1M.The good news is as you grow, your Umbrella pricing does not proportionately increase.This week we ran an Umbrella for a current client - $3M Umbrella over 32 locations throughout the US. 

I had a similar situation:  did a sub-to by having the seller establish an intervivos revocable trust, with my entity as trustee and the sellers as beneficiary. 

Similarly, we learned that just because a contractor has a higher price and a big business does not mean they will be professional or reliable in unexpected situations such as our local permitting process and sending in the proper forms to pass inspections.Only higher contractors that are references from trusted sources.

For that reason, it's common they will insist the Deed of Trust be assigned to them, they hold physical collateral, and their servicer handles the file. 

I'll admit it does take a lot of trust in your agent and property manager but some people are built for that.

We seem to be on the same page about everything and there is a respect and trust established, but they always say, "you don't need a contract ...until you need a contract." 

He will be getting a few properties on a deed of trust.

Definitely, get a lawyer, I don't trust you.  

Another simple deed change vehicle that will not trigger a due on sale, tax consequence or insurance problems (check w your carrier):  put the title into a trust. 

This will establish trust and allow you to become a stronger Wholesaler/Investor.