Make sure your agent communicates the reasoning why your offer is low (extensive renovations are needed, place is old, layout needs work, building permits needed, etc.). 

If you think it is 750 rent then that is what it is; the rehab sounds extensive and pricey.

Do you have extensive experience in the trades?

With being in Chicago, I'm not really looking to buy a property that would need extensive work.

My rehab model is usually 15 days for a cosmetic only with curb appeal, 30 days if you need flooring, trim, kitchen and bath updating etc, 45 if you add kitchen or bath gut and rebuild and 60 if you need extensive work or special order items like siding etc. 75 or 90 if you need longer.I sell my rehab clients on getting their house ready to stage a day before the 15th, 30th, 45th or 60th.

I have totally required a unit because of knob and tube — make sure it isn’t more extensive than you initially think.

I've also been looking extensively in Northern Utah, including Ogden, and will likely end up purchasing in the area eventually.

The loan technically goes into default if the 5 months are up and you haven't sold the the house, at that point you have a couple options;  you can give up and give the house back, you can make the extension payments which are HUGE and a big incentive to stay on track and get the property completed on time or you can get busy selling the house.

Because of extensive financials you need to properly underwrite a deal, I have found that developing relationships with the top brokers in your market(s) is a better investment of time/resources than talking with wholesalers..

I went into a lease extension negotiation meeting with the tenant feeling like a good guy for having cut him significant breaks on late fees and interest and also skipping annual increases for two years.