First it is critical to establish an accurate ARV that will be as close as possible to the Appraised Value when you Refinance the property.  

I'm also in the market for a similar multifamily property in my area so it helps a lot to learn from people like you.

3) Is the process of getting tapes purely a matter of establishing relationships with various sources?

I'm asking because I have not been able to establish a successful practice of inspecting tenant occupied units. 

Without knowing exactly what the costs to get the lot to the building stage, and then the amount to do the actual construction, plus all the costs for fees and permits, etc. you're guessing.

They established a new herd of goats, planted their gardens and settled their chickens in.

When you establish a relationship with the end buyer and build a rapport it may be possible, but that takes time.

I would presume the Chicago banks would have a much easier time figuring out the area, while on the other hand, it is much, much easier for me to go to banks around where I actually live.  2)  Since this will be my first property under an LLC (my owner-occupied is currently in my name), is there any benefit to having my current tenants (and myself possibly) start paying my LLC as a "management company" instead of me personally, in order to establish credit for the LLC?  

That is, either something that is a bit further out (usually East) and/or a bit smaller or in a less desirable neighborhood (like a 2 BR condo or townhome in say Anaheim, as mentioned) that is not yet your dream home but a place to build some sweat equity, to a large extent fix your cost of living here, and establish the beginnings of your local RE portfolio.

As for the LLC suggestion, I have been considering this but it seems to be a fairly common practice for newbies to get the first home under their own name then later start putting newer homes under an LLC once they're more established.