which triathlon?

So I've scanned and scanned the different triathlons in Iowa this year and since my #1 pick is not really an option anymore then I go to plan B.

Do I go the easy route? June 28th (sooner than later), a shorter swim (300 yards ) and the swim portion is in a pool versus a lake/outdoors. Note: cost $35 and is an hour and 15 minute drive away to West Union; and this race is different where you run, bike then swim.

or I do go the tougher route? September 26th (later than.. later), a longer swim (1/2 mile or 880 yards), swim in goose pooped George Wyth Lake. Cost: $75 and 15 minute drive across town; this race is normal with swim, bike then run but is also in my own playing field.

Part of me says this is a no brainer.. #1!!! but will I be disappointed in myself for the shorter swim distance? I've been swimming about 700-800 yards so I know I can do the harder race but then I have to keep training all summer.

Original goal: to complete a triathlon. But now that I've come this far, is it worth the extra 3 months of training, time, energy to say I did a harder race? One that I would be proud of? Or should I slow down a little on the crazy workout schedule, then kick it up again in September, then go for the gold at George Wyth? Or do the easy route and be done with it June 28th?

Hmm.. all these things to ponder. I have a couple of weeks before I have to decide at the June 28th one doesn't have to be registered for a few weeks.

Any thoughts?