They were all booked up and it took me 5 days to get someone out there.

I understand Philadelphia requires a local property manager. 

Maybe even a B depending on how you're feeling that day.

List my home for an isurance company who has a relocation service department 

Your lease should include a clause that the tenant is responsible for maintenance caused by a dirty filter.

By Friday—just three days after closing—it was listed on the market with professional photos.Over the weekend, offers started rolling in.

If I had to leave a takeaway from this post before getting too far in it would be that whatever goals are had you have, we have these goals for a reason and typically it does not go exactly as planned but even if it doesn't go as planned, we can pick up where we left off and give it a fresh start.

Yes, I'm a lender, but we have an arm that's been investing for close to 20 years now.

How critical was the lender’s turnaround time (e.g., 60 days vs. 90+ days) in your decision?

Quote from @Will Greenlee: I would agree with @Drew Sygit every software has its kinks and this one along with all the other ones started somewhere.. 7-8 years ago Buildium was less effective than it is today, and now it is a lot better.