And some markets that were overinflated will fall as well! 

A neighbor has brought to my attention that a dead tree on my new property is at risk of falling onto their shed and home and that I would be responsible.

I am not saying they are not important considerations but there should be more to your analysis.You also rattled off two NW Philadelphia neighborhoods in East Falls and Mount Airy.

Well, I keep hearing "if you find a good deal, the money will come"....like it falls from the sky or something...lol #4 Is true. 

Our occupancy rate has been higher this fall, using Airbnb and VRBO than it was during the summer and spring months, when we were listed on all 3 platforms.

Even though you plan to get a mortgage, the seller would likely treat this as a cash offer as you will close with cash on time if financing falls apart. 

but generally - new accounting and property tracking softwares fall short in one of two places: 1) they don't actually generate financial statements that a CPA or Lender will approve, or 2) They can, but the learning curve is so steep or convoluted it's impossible for you to get help if/when you need it (I imagine this is why this thread is a little slow right now)Have you asked your accountant what they think will work best?

Once interest rates start to head South will switch from BDC's to mortgage REITs whose underlying loan assets (agency debt) will increase in value as interest rates fall and should also generate 20 to 30% yearly returns.

And who will keep you from falling into any bad situations which happens often to newbies in the city

It seems you are falling for the alarmist rhetoric you’ve been reading and watching online.