I have a feeling this place is set up in a weird way, which I’ve learned is a pain to deal with.

They knew that changing software down the road would be a pain, so he bought the one he wanted to use out of the gate. 

It's not the end of the world if you have to start fresh but you will just want to be aware of that...additionally, migrating bookings is a pain the butt often especially when you have future bookings and/or deposits in their system.  

@Joy Shaw:Joy, I think you should change your name to Pain.

* If I identify a possible deal, is it bad form to reach out to the property manager directly and ask about the property's pain points?

I was a seller in a 203K transaction, and the reason no one wants to accept those offers is they are a huge pain.

Sounds like a few lessons will be learned and while it is a pain it is always good to learn. 

It is an absolute nightmare with the influx of inquiries to have to deal with a totally separate platform of communication and then makes it a royal pain in the arse to keep track of scheduling.2.  

If you can connect with investors and genuinely find their pain-points and can deliver solutions effectively and efficiently you will move closer to your goal of investing yourself.

Two tons that LOOK great on paper that I would not invest in are Rockford, IL (or Freeport as it is just as bad and next store to Rockford) and Clinton IA (where I own a 14 unit building I would be happy to sell to you that cash flows great and is an honest pain in the butt)...so on paper the Clinton property looks great, but in actuality it is not good: City is horrible to landlords, tenants have lots of issues paying, it is like Rockford where you feel it is the nicer part of town and then realize there is no nice partI would suggest you look at Iowa (anywhere but Clinton unless you want my place!)