If you want to go faster, double down and work 12-16 hours per day. 

My question is whether anyone has an opinion on if stripping the roof of the tar and gravel layer would be beneficial from a weight-bearing standpoint?

Secondly- imagine the person in the house not pulling their weight- once you serve notice to everyone in the house, that peer pressure is going to be the best rent collection leverage you have.

I could have taken some time off from work to get the rehab done a little faster.

Additionally, you can usually deduct expenses for the period in which the property was available for rent but not rented.A good CPA is worth their weight in gold.

Some could make the case that there are a lot of Sponsors out there that are heavily weighted in the C space. 

Paying contractors to get it done faster doesn't equate (I do hire them to get core systems and structures done right). 

But typically, lowering your housing and other expenses, will position you to grow financially faster, if that's your goal.

You’ll rent it for more and faster, by far.

Use a cpa to help you learn-get up on the learning curve faster.