Choices

I've always had problems with choices. Trying to figure out which of many options is the best use of my time or money or whatever. I can't have or do it all, nor do I want to. I'd like to not screw up and have to spend more of my time/money/whatever correcting the choice I've made.

Now is a time of many choices, which need to be finalized. It is race entry time. In the next month or so I need to go through a list of events for next year and decide which I'd like to do, can afford to do, and do without killing myself. I then need to figure out when entry for those events is, how to enter, etc.

Even after I go through all that, then comes this reality: I've never competed in these events, and many give preference to veterans. I could very likely get wait-listed and not get to enter my preferred choices. That means I should possibly try to enter more than I can possibly begin to afford to enter/complete/travel to.

There's one event I'd love to do one day, but I don't feel like I'm ready to tackle it yet, however every year the odds of getting a spot at the start get worse. Should I even think about trying to enter, when I know I'll chicken out? What about events on conflicting/consecutive weekends? Knowing I won't likely get into every event (or most for that matter), should I really load the deck that way?

Many of the paid events I have a better shot of getting into, but once paid, I'd hate to have to drop out due to lack of funding for the trip.

Any sage advice? Or does anyone know of any events they are thinking about doing, so perhaps travel expenses can be split?