You will NEVER time it perfectly, and waiting a couple years for the market to crash is dumb when you could have been getting cashflow the whole time. 

I was wondering what is more detrimental to structural: standing water for couple of days or rain pouring in over months?  

We are evaluating investing in a couple of Brewerytown, Philly 3 unit shell properties.

Find a couple hours to read "White Coat Investor" and "The Millionaire Next Door"

So, find a couple of good quality GC and build relationships for the long game.

(We got the mediation cert and had a sale date in April, 2018, but the borrower filed BK 13 a couple of dates before the sale.)

With her focused on the almost limitless upside of REI, I'm positive that we'll get a couple of deals knocked out this year. 

Some appraisers will work with you more than others will; so my advice would be to ask a couple property management companies or local investors what lenders they recommend. 

You have lenders saying sure "6% with a couple points" and that isn't good enough.

Maybe you need to focus more on social media marketing in your area (Facebook, Instagram, etc...) or maybe you need to expand your reach and look at other markets slightly outside your area.3) Maybe try finding someone to partner with who has done a couple deals so you can at least get part of the pie.