I show up and he is shocked beyond belief.

With all the recent changes to the housing laws in Cook County, it would not shock me.

Your agent schedules the inspection for 4-7 days, but the initial walk-thru is to verify condition and keep you from paying $500 for an inspection if there is a fatal flaw with the property...all identified by an experienced agent with construction experience.You should be doing a de-brief after the walk-thru and building a preliminary scope of work to estimate your renovation or repair costs. 

If you have the chance to do a preliminary consultation with this person, you could ask them to give you an overview of the home buying process in that area, local issues, what the current market is doing, a skim over what the contract looks like, etc.

With that kind of money, I would be shocked if you couldn't find REI (1 or more deals) that would get you a much higher CF than $450/m plus what you could get with the $120k cash out if you refi.

I also am betting on inflation, so it wouldn't shock me to see rents of $4000-4500/mo in the next 5 years or so. 

Just had done a few preliminary meeting with city and wanting to move forward as well.

This will allow you to get a realistic understanding of what you can/can’t afford and a baseline for what you need to do to improve you position and any additional capital to save.  2) Lenders will request the below preliminary information.Name of entity (organizational chart if applicable)Personal Financial Statement (PFS)Schedule of Real Estate Owned for each borrower/guarantor (SREO)Resume/Bio for each borrower/guarantor, if applicableBank statements for verification of depositsLast 2-3 years of tax returnsI recommend using a mortgage broker in your area that is able to connect you with top commercial lenders to get you multiple competitive offers.

I have been a little shocked that about half of what I got is telling me I am wrong or that what I have already done is a waste of time. 

Having heard numerous complaints through the years, you would be shocked how many people openly admit it in the hearings without even realizing.