Also, what can I expect to pay for all of these permits?

I'd be in one heck of a situation if I had all of my units go vacant for a month or two, and expect to have that money to pay expenses...and no safety net.However, what if you could take your side of the equity and find your feet. 

Why did your deal fail or not meet your expectations.  

-Rentals are very labile - some rent in less than a week for more than expected, others take two months or more despite being listed for less than they were previously rented for two years ago-There is no cash flow in A or B for new purchases unless you want to put down 30% or more, or find a unicorn deal.

Expected to hold 3-5 years and then sell for nice ROI (greater than 35% cash on cash return).

They're all good answers that matched the "it depends" mentality that I was expecting.

This is where most projects go south....If you and your Contractor are not on the same exact page regarding what you are expecting to receive and they are expected to provide, then you are doomed to fail.

It is hard to think about giving up an "asset" that is worth $1.15 mil and at the low end would be expected to grow at 5% per year (house worth ~1.7 mil by 2035), even if I incurred ~$50K worth of costs over 10 years. 

What are you expecting to rent it for?

These all factor into how long a tenant stays and what vacancy rate you should expect.