I'll make sure to utilize as many tools found on this site to ensure I profit all the benefits it has to offer.

Recommendation is to back-roll after you apply the paint to ensure even coverage and sheen. 

From the insurance side of things, I would explain that his role as the "bank" in this transaction would be to ensure that insurance is carried, which he can do by being listed as the lienholder, mortgagee, or additional interest (all the same thing) on the policy.

. - they will give you both a contract to officiate the sale between the buyer and seller (no need to make one up yourself although i have done so, many free ones available online and if your half decent at contact law it is not that complicated to make it legally binding, your title company would review it  anyway to ensure accuracy.) - they will coordinate with the buyer for appraisals, termite inspections, coordinate with their mortgage lender, earnest deposits, etc. - they will be the primary contact, so after you and the buyer have settled on the price and contact a title company, they do all the rest of the work!

I also offer them to double list the deal if they want it to move more "efficiently".  

With the duplex my wife and I own, we have always been upfront about being the owners, and we try to just manage their needs/concerns as efficiently and timely as we can!  

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I might ask for a contract (tell him to black out the price), just to ensure he isn't trying to jerk you around.  

I'm looking for something that I can hold for the long term and is already running efficiently.

Our lease states that we can check smoke detectors monthly to ensure they are working.