You deserve it for going through what the DOB does to our city homeowners.

I’d hire the structural engineer for a little extra money to be sure and call it a day!

Because of my lifestyle cutbacks, and now that I have some phantom cash flow coming in to pay part of the mortgage, should I cutback from 40 hours a week, to work on more productive things like the real estate investing, or should I keep working the 40 hours and keep putting the extra income away for a while longer?

If you used your investment money to pay the $36,000 you will have the entire cashflow of $500 per month for 60 months = $30,000, but if you get the loan you will be paying out  $230 per month extra for 60 months =  $13,800 extra, or a total $730 x 60 months = $43,800.For 8%, I would play it safe, keep my cash tucked away since it is very difficult to work and save $36,000 in one wad of cash and use someone else's money for such a low rate.

My wife and I have been throwing extra at our student loans but have also house hacked and purchased 1-2 properties per year the last 3 years so it is definitely possible to do both.

However, that cost to get into one could definitely kill this strategy (at least where you currently live).Since the numbers make sense for SFR (make sure you check occupancy too), this seems like a great way to generate some extra income from your current home.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it.We have a 12 page management contract that we've added our real experiences to over the years, with the intent of protecting both us AND the landlord.

Should we just collect a little extra each month until they have submitted the full last month's rent (and of course have the specific payments and what they're for outlined in the lease)? 

In this hot market it seems like this makes the most sense, correct me if im wrong but the value in the quality of materials and brand new everything is probably worth the extra money in the long run.

For example, you could see a property on Zillow that pulls great numbers based on the Airbnbs nearby, but all of the Airbnbs have pools and yours doesn't (which will cost you an extra $50-100k on top of the purchase price).