I have always avoided inadequate parking for our multis & it's paid off.

A oral contract is still a contract.These situations very rarely work out.I would insist on getting all copies of all utility bills (from A or the utility company) and when leases are up average the cost monthly over the eyear, raise th erents accordingly and put the utilities in your name.

Any rent control from government or all free market?

Acceptance of rent from someone constitutes a legally binding, oral lease agreement.

Should I just always assume I'm going to need new floors throughout, new cabinets, countertops, appliances, most or all of the light fixtures replaced, new paint in and out.

For example, home purchasers often include a contingency that specifies that the contract is not binding until the purchaser obtains a satisfactory home inspection report from a qualified home inspector.contractAn oral or written agreement to do or not to do a certain thing.conventional mortgageRefers to home loans other than government loans (VA and FHA).convertible ARMAn adjustable-rate mortgage that allows the borrower to change the ARM to a fixed-rate mortgage within a specific time.cooperative (co-op)A type of multiple ownership in which the residents of a multiunit housing complex own shares in the cooperative corporation that owns the property, giving each resident the right to occupy a specific apartment or unit.cost of funds index (COFI)One of the indexes that is used to determine interest rate changes for certain adjustable-rate mortgages.

Usually the ones who know one or two will know most or all of them.

It's true for many Americans - in fact, the man who created the 401(k) in the 70s regrets it, because it created a false sense of security and many will indeed find their retirement savings woefully inadequate.

I know that I will only occupy a unit for a limited time, and the house-hack is just a way to get more favorable rates, better loan terms, and elminate, or severely decrease my housing costs today.I am sure there is someone on BP who has built some wild spreadsheet, or other model where you can actually calculate the value of no mortgage, but for me, as long as I am covering most, or all of my PITI while I am occupying a unit, and the deal works as a stand-alone investment deal, then I am done running numbers. 

If you're looking for additional safety, you could even split some of it to be invested into conservatively underwritten debt, so that if things go badly you can foreclose and recover some or all of your principal.