From there, he/she will be better able to assess your needs and offer advice about remedies better than any of us here.

The assessment ratio will differ depending on your property classification and the equalization factor is the same throughout Illinois.

There is not much issues with the building, I have seen their budget and dates of major repairs/ life expectancy, potential special assessments..etc.I guess I don't want to overpay for it, but the same time if I was going to offer $62500, extra $2500 it is not a huge deal.

If the assessed land value is higher than your offer, I doubt the bank will send out an appraiser.

Without reviewing the documents, it's really impossible to assess the efficacy of the seller, the syndicator or the asset/collateral.You're considering funding a real estate deal that happens to involve probate. 

And what the taxes were last year/what it was assessed at/could the assessment change if I purchase at XXXk?' 

As I progress through the MLS with my agent, my opinion is bound to change, and I will adapt.

The idea that you will be able to "predict" the Path of Progress without having "insider information" is difficult.

I greatly appreciate that and will keep you updated on my progress.  

I've reached out to roughly 10 financial institutions in my area so far- I will keep calling to see if I can make any more progress in terms of finding an REI friendly lender.