Then, even if you get the loan you are limited by debt to income ratio ? 

Right now All of my real estate investments focus on investing in turn key properties and becoming a limited partner in syndications.

Is there maybe another workaround to this (hiring an agent in some sort of limited capacity?

Our concern is that if he wants to contribute, lets say 40k, that he would have to withdraw considerably more than that due to the tax hit. 

I've had limited success with this, and you may get someone to give you more specifics on timelines. 

I did limited research where to move, but I absolutely knew we didn’t want to live in IL and pay ridiculous property taxes ($850 p/mth, 2,200 sq ft home).

I sometimes drive in excess of the speed limit.

Get those CCs paid down, and you'll also potentially earn higher credit limits on those existing cards (a good rule of thumb is to keep your utilization lower than 30% of your limit which, if done consistently, can boost your credit score). 

Here they have overages if you go over your limit in terms of how much you can download.

(Home Equity Line Of Credit)A line of credit would give you the security you want without having to make payments or be charged interest unless you actually need to withdraw money.