Nothing to be concerned for.

Mom and pop investors are known for being more flexible when it comes to the many unique situations with concern to tenants.

He's not concerned with getting top dollar. 

Being a shorter repayment schedule as well as higher interest, it looks like the HELOC would take a good bite out of one's cash flow, and that it is only a temporary solution, not a permanent one.

It may not be a big concern?

As far as the signing then a trustee typically signs "in their capacity", something like this:Joe Smith as Trustee for the Bill Miller Living TrustEscrow probably would not be concerned with "...that these 3 are the owners of the trust?"

These two will be at different banks, but my concern is that the banks might not approve either one of them if I do it at the same time.

As far as pay is concerned, I get paid weekly now .

Is this something we should be concerned? 

If he doesn't, I would start to become concerned about why this simple possession case is taking so long (3 months for an eviction case with no clear end in sight is long in NH in my experience, unless the plaintiff messed up something procedurally).