There are plenty of regional pilots that essentially fly part-time, and make their real money with a side business (real estate, insurance, consulting, financial planning, etc). The key to this would be go somewhere with work rules that allows for easy dropping and/or manipulation of trips. It would also be important to find a company with bases near your home if you cannot or don't want to relocate.

The people I know that have 2 careers have lots of cash but work their asses off, and come to think of it many of them are in their late 20s-early 30s and single.

Your mileage may vary.