I spoke with an escrow and title company, and they informed me that they need an executed contract and the probate paperwork to get started.

You are in the right place, soak up all you can from forums, podcasts, books and then pick a strategy to execute on

Also, it sound like price includes them processing the plans through plancheck, which requires their staff time. 

I'm watching for trends regarding tenant complaints about management/staff/work orders, etc. 

When we move in, we would pay this family member a FMV rent under an executed lease.

If it's a larger organization, feel free to inquire about their different staff qualifications.2.

I know some of my colleagues better than others, and I know for sure that we do NOT run the same operation.Some CPAs/EAs are one-person home offices, and some are multiple-office firms with several accountants and supporting staff.

I have had clients successfully execute the rent by the room model up and down the front range.

They area business and they have the staff to pay, need to be fairly compensated for their efforts for putting this all together (its a ton of work).   

2) you’d execute a deed from the llc to you, and record it.