The fact that you described this tenant as "a good tenant of 5+ years" is what I would focus on.

A lot of the basis of my position on this can be described as “gut feel”.  

Yes that’s what I was initially thinking… then I started to structure the deal in my head and it looked a lot more like what you described with a partnership.

Once you are familiar with what a good investment looks like, then you can create a rule of thumb to help you analyze property faster and only dig deep on the ones that look promising.Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...

Ive known Dave for years now, and the one word Id use to describe him is Integrity.

Hello @Yvonne Wang,The scope of work should include the following:- Basic info: Property address, client name, contractor's contact info, address, license#'s, signed general/operating agreement b/w contractor and client- Specification of repairs: Repair item, Quantity of items needed, total & per unit cost of items, taxes (if applicable), Completion hours, title of the person responsible for the repair item, written summary describing the work- Add'l info: Schedule of repairs, additional payment schedule details i.e. disbursement schedule, method of disbursement, deposits, holdback amounts, etc.The screenshot below highlights a couple of repair items.

but not as described above. 

Additionally, it feels the most appropriate approach for both profiles I described above and allows me to focus on learning one strategy.

Cash on cash describes how much cash a rental property is putting in your pocket on an annual basis divided by the cash you took out of your pocket to buy it. 

The early portion of my career was buying turnkey rentals, like the one you described.