Ultimately it's what is the return you are getting versus risk,capital deployed, and what is the timeline and headache to achieve it?        

Clearly my ultimate plan will be to hire an attorney to create this structure, so if anyone know of any that specialize in this (preferably in NY/ NJ/ Phila metro area), let me know. 

Here PM companies are expected to provide routine checks of properties, both the commitment and cost are baked into the service offering - so ultimately the client pays (PM fees are typically 7-10%).It still falls short of what we do in-house for our own properties (one of the reasons we are growing our own capability).  

Ultimately, you are the only one who can decide what amount of risk makes sense for your life, but there is no argument of which strategy, mathematically, is a better investment. 

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I have been considering if it might be better to BRRR as Buy and Hold is my ultimate goal long term.

sounds like you have a great opportunity. i recommend the contact for deed route. as you mentioned you can get a lower down and more flexible terms. if you can get a 10-12 year ballon payment you should have no problem refi'ing out prior to that with a conventional loan and pay off owner contract. i would try to get the per unit down. you could try to show the total amount you would be paying when you add interest into the equation and see if he will come down on asking price, at least to market if not below. as well as play up the continued cash for with zero management headaches. ultimately if it cashflows well and you have good fixed debt for 10 plus years my experiences has been that price per unit is less of a factor. cash flow is king.

Ultimately whatever you end up paying for the property is going to go into your equation to determine your cap rate.

My ultimate goal is to work 2 days a week by age 45!

Ultimately, it depends on what other rehabbed properties look like in your area and what they are selling for.