Should I wait to have these items done before signing the contract (could take weeks) to give time for home inspector to inspect the property (and risk another buyer over bidding me), or just sign the contract and have the home inspector come when everything is done?  

Buyers often have trouble picturing what it will look like with furniture. 

The risk of waiting is that some other buyer can swoop in at anytime even in a slow market and get that property in contract for a price that you would've been willing to pay.

At the moment I just have the pre-approval from a bank, so I can search for properties and realtors know I am a serious buyer.

I'm a cash buyer.  

We now only let our "qualified" buyers know the address so that they have to have specific information provided and verified by us.

BUT if you are going to flip it....the buyer is going to ask for the roof to repaired.  

Any chicagoland area wholesalers or buyers who can help ease my worries? 

You could help her make some of those connections on BP by hunting down the movers and shakers in whichever markets she prefers. 

I want to become a private lender for a buyer of a condo in Orlando.