Hi Rodney,
It's been eight years of tri for me, while keeping up a steady running/ marathon schedule. Agree that for everyone it's an individual approach- but have found the following to be useful:
1. I prefer quality over quantity for races- usually this means signing up for a handful of races that are either in really beautiful places and/ or nice course/ competition. I don't do races every weekend just because I would get bored of them.
2. I stagger my distances- usually going from shorter to longer. So each one becomes a bit more challenging, and I have not thereby incurred an excessive injury risk from a longer race, with a shorter tri following.
3. I have ended up with some "race congestion" so tris 2-3 weeks apart- on different continents (goes back to #1, no I am not a high paid pro) but this is useful because to the extent that racings requires a lot of basic logistical prep- I find it useful to get it all done in a nice coherent block, and then vacation carelessly over the summer.
4.Once you start building up race distances (which is what it sounds like you want to do) scheduling your training because even more fun (read logistical nightmare) so in the process, you might find it preferrable to schedule fewer races or better tailor them to your schedule and whatever non-tri life demands are.
5. Book massages! Very important for avoiding injuries and contributes to overall happiness. I have done this as part of my training schedules (everything from marathons to IMs) and knock on wood 8 years no injuries! Injury avoidance becomes a key theme in training for longer tris. And as mentioned in #4, as you get to longer tris, the shorter sprints probably have less strategic value in your overall training.
Happy racing!
n 