Keep in mind if they get turned down again for the loan you will have to give them their $500 earnest money back.What you might want to consider is tell them if you do give the extension for them to try alternative financing options you make the $500 no refundable regardless if the loan does not go thru.  

That means having a solid understanding of the work flow, documents needed, alternative steps to take if need be.

As an alternative, you can probably insert an early termination fee amount so it provides flexibility for the tenant to leave without having to deal with subleasing issues; however, you'd have to consider worst case scenario: Tenant exercises the early-termination option in December, which places you in a tough situation as a landlord in the Chicago area. 2.  

This may be the less painful alternative.

If you don't have a job yet, focus on getting a good one first (unless you have lots of cash and or access to private funding and can buy property using "alternative" means).Step 3 - Play with some numbers to determine how much of a mortgage you can afford.  

Qbox is a safer alternative to Dropbox since it is specifically designed for Quickbooks files.

As mentioned total budget for Rehab is around $85,000-$110,000 unless someone has alternate suggestions?

Just wanted to seek other's opinions on this and see what other alternative solutions are out there from here on.

Could be a great alternative to Hard Money.

Alternatively, if you don't want to take the additional hits to your monthly cashflow, you could consider refinancing the loan to make the loan "cheaper".