I am leaning more towards a tri or quadplex (Fort Worth, TX) since I have been hearing it takes the same Property management skills as a duplex and generates cashflow every month besides the duplex would just be covering my rent, don't get me wrong I would absolutely love that just starting off as well... but would rather have the extra cashflow coming in to help put towards another property ASAP if at all possible.

This way everyone wins-- you get the increase, it's on the lower side, and if the tenants get to pick the upgrade-- they will be happy knowing where the extra money is getting spent.   

Definitely not worth the extra work.

I’d be saving an extra $700-$800 / month.

Now, that 4/2 is a bunch of extra space that a single person does not need, it's just extra crap to clean/maintain/etc.

If you plan on keeping the house long term spend a little extra and don’t go with the cheapest shingles.

In short, I recommend never to take all the extra cash flow out of the business, not only to be prudent with the NOI, but also because you need to operate a profitable business. 

After inspections I was able to get another $8,000 off the selling price to account for extra labor that would be needed to fix the place up.

Are you going to diligently pay down that consumer debt once you have the extra cash flow? 

If you are dead set with tackling this project solo then I suggest you factor in a decent amount of contingency cost and extra time for the project to run over.