With all of the reading and podcast, I have a big brain of information now so the biggest struggle I’m encountering at this time is where to start when it comes to analyzing.

I am the guy driving that truck you may have seen that sported the bumper sticker that read " Hungry?

Dealing with brick foundations, homes built in the 1800s, was the biggest challenge we encountered.

Because you veered off course, you encountered a side business that you're willing to leave, but sounds like you did well with it and that you might even make some money on the sell of the property.  

So those tenants will leave and encounter higher rents.  

If all the agents you encounter "just fill out forms", then you may decide that this is not what you want.

Personally I have encountered quite a few seller-financing options with decent terms recently.

Even if this house is brand new you will still encounter issues.

In those three months I’ve encountered numerous issues with the condo (leaking drain, Furnace repair, AC repair, and a few small issues).

Tough to tell age of those AC things w/out photos of the model , serial number, the sticker that looks important, lol ; If you already had the home inspection, did they comment on it?