You're getting more in rent per month, so if you want to take that first couple months extra and sock it away for just in case, I would do that.

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When I sell it, I will keep my mortgage on the property and owner-finance it to the buyers.This generates at least an extra $50k+ on the deal in interest, but even my own insurance company isn't sure how a claim would be handled.I HAVE to keep my insurance policy on the property according to my lender.

When asked they told us that closets, trim, and doors are normally extra cost during turnover painting.

I also have an t5i but the Ricoh you can put in your back pocket and works great for wide angle real estate, so it was worth the extra few hundred for me.

We could put the extra $200k back into the place in adding a laundry or converting a garage to a studio or other upgrades. 

Adding in an extra bedroom if possible?

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.