She currently rents it out and owns it free and clear but is a tired landlord. 

Further, if you decide to sell that property and reinvest into another investment you don't have to do the 1031 exchange since you are doing so inside of a tax-sheltered vehicle (IRA). 

Is it more cost efficient to claim miles on your own vehicle or purchase one with your business and deduct that way?

This is not true and I will explain why.Can you provide a realistic annual maintenance cost that applies equally well to the two vehicles below:One is a new economy car and the other is a wrecked Humvee.

I hesitate because this opportunity requires a $3,000.00 fee upfront to prevent tire kickers/time wasters.

You can spot these by really nice lifted trucks with big tires they provide white glove service with expensive pricing.Good luck!

I got tired giving away my good deals to other flippers.

Most tired landlords like the monthly and tax benefits of spreading out the gain over time but are tired of the tenant headaches. 

He called me up Friday stating he was going to a Gala in NY and he wouldn't be able to complete the project until Monday then called me Monday to say he was too tired and would be there Tuesday.

Please be sure because Im tired of hearing "no, we dont manage east cleveland" after wasting your time with them.But, Ill be happy with any help.