So, you should be looking to understand the labor and material costs.Material is usually easier:Anyone you hire will need: drywall patching materials, sanding blocks & paper, primer, paint and the corresponding paint rollers and brushes.Labor may depend on level of skill:How long will it take to prep, patch, sand, prime and paint?

To address parking, one tenant blocking in another in the drive and the late night calls it produces has led me to this policy.   

If the tenant identifies an area of moisture that may be causing growth we immediately address the source of the moisture, replace and damage building material (usually dry wall) and or use mold cleaning solutions/mold blocking primers as required. good luck

Off the top of my head a win we are proud of is bringing back a few blocks on the SouthSide of Chicago. 

Also, is there some prevision I can put in the lease to prevent the tenant from blocking the drive access to the ADU/Boat and from physically messing with my stuff, such as a fee.

Memphis is a block by block city, so be careful to get your comps from very close to the subject property. 

Experience – I want a lender who's been around the block and knows how to navigate challenges.

"Maybe" 10 blocks. 

Build site is a block down from my house, so I'm planning to manage myself.

Balancing work and income requires using systems like CRMs and time blocking.