Would I be able to run you through my high level plan to see if we’re spending time in the right places to expand our online presence?

The lender has all my paperwork, but waiting on the appraisal info.Anyway, once I gain everything I need, I’ll be close to ending the tutorial.In order to reach level 1, I MUST buy the property and it MUST cash flow AND appreciate.  

With a residential property don't you have to put the property on stilts or bring in fill and compact it until the 1st floor level is at or above the zone base flood elevation?

Can I level the existing property and build a 4 Plex in its place?  

@Ben DanielMost commercial lenders aren't requiring an LLC, although at your level with the number of properties you have, an LLC would not be a bad idea. 

I am a native of Chicago, but currently living out of state- looking to purchase back in the area within the next year or so, and would love to connect with a "team" who could be my eyes and ears for a potential deal if I purchase from out of state before I relocate back. 

No matter how much of a livable space it may resemble, if the basement or garden level isn't legal habitable space, you are taking on significant risk renting it.

But yes you hit the nail on the head, most are very basic level.

You have to take into account the level of service provided by that company.

You cant get the same level of detail through other methods.