My question is this... on any subsequent purchases where I'm pulling more than 50% of the weight, how much additional percentage (assuming 50/50 downpayment) would the other legwork be worth... 55/45 or how would the legwork typically be reflected in the deal.

Most junk removal service prices will pay for labor, transportation of dumpsters & junk, as well as dumping fees which normally go by weight. 

The one I own has snow removal, grass mowing, and common area upkeep and costs $70/month for HOA's.  

The builder didn’t intend on so much weight being added later, as it’s only made to park a couple of cars, not a whole second story.

While I agree 100% that taxes, insurance and other upkeep are expensive, if I rented I'd be paying a landlord a sufficient rent to more then cover these amounts in nearly every instance, plus his mortgage principal amortization.Since, personally, I prefer a home that is nicer then most rentals and like the idea that the home is mine to do as I please, I choose to own.As a RE investor, with over a 150 paid off doors, (antithetical to you Joe, I'm aware) I know how to purchase RE at a discount.

I can't imagine any auditor worth his weight would allow that.This is a situation where if it sounds too good to be true, it probably is.  

Keep in mind they weren't built with the intention to hold that kind of weight.

Verbal conversations hold no weight. 

There is zero incentive for landlords to do any upkeep especially with long term tenants since they are all below market. 

Depending on were it is, a dock permit isworth more than its weight in gold.