Eager to learn about RE tax write-offs, how to document/keep up with expenses, what can be written off, etc. at this point...However, the 3 RE focused CPA's I've visited with want $5,000 annually for a couple hour sessions a year and a few recorded classes and other resources, which does not include tax preparation. 

So, you are simply suggesting get my, “hands dirty,” with Long term rentals, rinsing and repeating the “house hacking” strategy before even considering STR’s and meeting REPS and Material Participation requirements to maximize tax write-offs on my future W-2, correct?

Under the partial disposition rule, you can write off the not-depreciated value of the old roof.

I've heard from other people in the group that you might get one good person out of 30 that write with interest. 

Depending on the cause of the taxes it could be offset with write off's, deductions, carry overs, etc.You could always take out a loan through a cash out refinance to pay off or down the lien.

@Colleen BaroneAs @Nathan Gesner Mentioned you are supposed to but in reality 9/10 deals that get sold in areas with a POS will not have a POS report provided prior to writing an offer.

I thought about writing letters and posting through the letter box of the nicer small multi family i see, but i understand the owner likely doesn't live there.

I would do it for the tax write offs, as well as another positive for the resale value. 

Before filing such a complaint with DHCR for breach of the warranty, the tenant must communicate in writing with the landlord about the problem.

The tenant has not met the requirements of withholding rent.If the tenant claims they have moved out, ask them to state that in writing (email or text is sufficient) so you can enter, remove their belongings, and take possession.