I scoured craigslist, the web and facebook for people to do very specific tasks.

You are right about dark web exposure.

I know that ideally, I reach out to my broker or any other reputable insurance provider to get a more accurate estimate.

They seem to be a reputable company, but nothing beats personal testimonies!

They'll probably also want to be sure that you are competent to operate the property afterward, because their reputation is tied up in who they do business with, and it's bad for everyone if the property becomes devalued.

You want to find local home buyers with overage who wholesale as they are usually more reputable.

Almost every reputable lender is going to have a draw process for any lender funded rehab portion. 

As I explore the neighborhoods in NW Philly, any suggestions on reputable agents with experience in those areas? 

I like working with lenders who are familiar and reputable in the market you are investing in.

Lol, every single time I've decided to do the painting myself........about halfway through I am regretting it big time......my body hurts, it's mind-numbingly boring (I think that's why painters have the drinking/druggie reputation... :-)