Had several challenges with their bookkeeping after I had to make an adjustment to one of my monthly payments.

Challenges?

In a city like Philly, you will face many challenges - you need to learn the market and know the neighborhood and the block and make sure all of your numbers are within reason, you need very reliable contractors, you need a to understand the permit process, you need to be familiar with market expectations. 

The biggest challenge is time to manage a property.

In my experience, finding cash-flowing deals on-market can be challenging here (1% rule can be hard to find) but not impossible.

Weekdays are particularly challenging.

So, I am truly coming into this blind... but excited and optimistic and ready for a new challenge/adventure!

Combine this with interest rates that are near the high for this century and cash flow is challenging.  

Challenges?

Starting with a smaller property or a few fix-and-flip projects can help you build equity, gain credibility with lenders, and better understand the process before scaling up.Securing funding for larger projects can be challenging without prior experience, but options like hard money loans might be worth exploring.