We experienced both ways. Oldest son was coached by myself or another LL dad (again pulling the all-stars) all the way through 8th grade (13u) usually playing up an age group. After that we joined a "smaller" program for 1 year, and then moved on to a larger program for 15U-18U. Ended up getting 3 JUCO offers, smaller D2 offers, and 2 D1 offers. I loved coaching him, and the time we spent together. We used to complain that we had to drive 30 miles for a game.
Youngest son played LL until age 9 (with me coaching) until we moved to a smaller community that did not have a good LL program. He then moved between larger programs for 3 years playing up a year until 13U when he played on a fully funded team for 2 years. Since then he's been with one of the larger travel programs in the area. Started as a freshman on a top 5 team in Texas and we hope after an injury to have a great rising Sr summer. I loved coaching him when he was little and missed doing it when he would have been old enough to "talk" more, but I realized that he needed better coaching/team than I could provide (walk on college). I'd love to drive "only" 30 miles to a game............as sometimes our "close" games are 90 miles away. Get lots of car time although 50% of it is spent with him on the ipods and me listening to a game or sports radio ("you can only talk so much dad").
There are more than one ways to skin a cat, you just have to make the best of it.