I think sooner is better.

I will be in a much better financial position if I choose to do this after the 60to 90 day period.  

Do you think it would serve me better to invest in a smaller and more affordable area like reading pa?

A lender may also want stronger debt coverage ratios and be tougher on appraisals because they will have more work involved securing several  properties if things go south for any reason.Your loan amount is rather small for a blanket loan, you should have better luck with a small lender/bank or regional bank as many larger lenders may want a minimum loan of $500K or 1M.  

It's a team sport, and my partners and I leverage each other's skill sets to do a better job than any of us could do alone.

For illustration purposes, the majority of investors who post on BP will move the property that pencils as a true BRRRR to the front of the line over the better situated asset with better fundamentals merely because they receive 100% of their invested capital back as opposed to 90% (again numbers are merely to illustrate a point).

I think white would look much better, but I am worried that's going to be a lot more work and I also fear how well the white paint would hold up over time (they are rental units I know they'll take a beating and potentially chip/ scratch).

Does anyone else have a better solution?

I've heard of "blanket mortgages" which I thought might be a better option for me so I could use the equity in both properties and only need to get one mortgage.

I mean, that's about half the value of a better Canton house!