I have spent hours searching the forums and listening to podcasts. finding tidbits here and there but nothing comprehensive.

Neighborhood Scout - Gives you a good overview of the areaCity-data - Use the map view to zoom into the specific block and it will give you more stats than you know what to do with.

CLUE (Comprehensive Loss Underwriting Exchange) report.

Is there a comprehensive list of expenses to consider to ensure I don't miss anything (taxes, insurance, fixes, etc...) when calculating rent to charge? 

I will meet with at least 3 or 4 of them in order to get a better overview of the city.  

Hi @John ThedfordThank you so much for the comprehensive answer.

After having gone through getting a contractor to come in a put together a comprehensive bid of the project he came in 38k over his rough estimate on the high end.!

PA doesn't have many specific landlord laws, but definitely ave a look at http://www.nolo.com/legal-encyclopedia/overview-landlord-tenant-laws-pennsylvania.htmlPhilly does have some additional ones including a business activity license (they want you to pay taxes), rental suitability certificate (which certifies you have smoke alarms and in theory they can inspect, but never do).

I know that's a very general overview, but there are literally areas in the city where crossing a street or two can take you from a B to a C or C to D.

I have been listening to many podcasts, trying to get an overview.