@Zach Howard there is no agreed upon Classification in the 1-4 unit market.We've done our best to logically create a system for our market, mostly based upon relative sale prices, but also using crime rates, rents, occupant income and a few other variables. 

Pay the bill yourself, then reimburse yourself by charging the tenants based on a formula.

I think I'm in a pretty unique situation and am trying to figure out the right hoops to jump through to move forward.Long story short, I'm trying to tap into the equity of the rental property passed down from my grandparents that is held in an S-corp which is co-owned by myself, my siblings, our cousins, and an idiot uncle.

while i do think it's valuable to analyze properties, it's really difficult to underwrite based on photos. 

Jump in!

In addition, education can only teach you so much - what type of experience-based learning do you receive when joining these teams? 

I can’t diagnose your issue from the pics (though it seems repointing needed) I can say that there are contractors in this area who will immediately jump to the $35k+ solutions when they see deferred maintenance on these types of foundations.

Value is based on each individual and they will need to determine if they think there is any value.

I'll jump on board with the others. 

To be successful in any business you have to let go of that fear and jump in with both feet.