Personally, I would suggest aggressively pursuing your 4-year degree first or at the very least along with acquiring your ratings. This is invaluable education for running your own business. Major in some fashion of business or finance. Don't wait - get 'er done.
It's great that you're working with your Mom, she brings experience to the table and allows you the time to do these other things.

After reading your post I'm not sure if you have really defined what direction you want to pursue with your own career ambitions. Have you?

If your goal is to expand your freight operation, then keep your eye on the goal. Do everything in your power to learn that business from the inside out. If you are looking to learn the business from a pilot perspective then pick the company you consider to be a good role model and plan your steps to get hired by that company - for the purpose of learning their business model and operations. What are their minimums? What do you need to do to achieve the minimums?

I don't think shooting to be hired by FedEx or UPS would be a good goal unless you are choosing the path of a career pilot (it will simply take too long for you to get there) - - Define your ultimate career goal.

So, if you are looking to learn the flying operation of moving cargo for the purpose of expanding your own company (that is an important distinction) then start looking at companies where you might be hired in the not-so-distant future...AND that parallel what your own company does. Ameriflight, AirNet, etc.