I share in your frustration. DH and I do a lot of the same events as well. And now is the time to start registering for all of our events.
Chicago Marathon: $220 (not including transportation & lodging)
X-Terra Blackhawk Tri: $110
Iceman Cometh: $130
Stark Raving Mad Adv. Race: $120
Tour of Cedar Creek: $75
Owasippee TT: $50
Pendalouon Trail Run: $50
Block 58 Tri: $150
. . . and there are more . . . We have a monthly budget for events.

I was really upset when DH and I spent $180 for our first Triathlon last year. We showed up race morning to find out we were dq'd because we were literally 30 seconds late to checking in our gear to the transition area. I could vent about this forever because it turned out we WEREN'T late according to their own instructions. And they never refunded us either. Grrrr. That organization is now being sued by a national triathlon association

Anyways, the point is, racing is expensive.