I look for different things for different events. Last year and this year, my A event is BWR SD because it’s my hometown event and I like that it’s competitive. The course is challenging, fun, and now familiar to me.
For other events, I like a bit of novelty - so if I haven’t done it already then, I’m more tempted to make a drive, or even a weekend out of it and pay some money. Last year I did Rock Cobbler 10.0, and it was pretty epic, fun and weird, and very hard. It was actually too hard and now that I’ve done it once, I’m going to skip it this year. It’s an entire weekend and quite costly given my circumstances. I got very muddy, shoes were soaked - which is something I’d like to avoid, and my back was killing me for a couple of days after that. But the novelty drew me in. And I had a ton of fun with other cyclist that I know from my area. No regrets at all.
Speaking of novelty - there’s a local ride/race which isn’t too expensive, it’s a reasonable distance and I haven’t ridden there before so that made my calendar. If it’s totally raining that weekend, I’ll skip it without a thought and since it was “only” a hundred bucks I’d rather stay healthy than get my money’s worth and wreck myself or my bike.
When it comes to courses, I know it’s going to be difficult in some shape, way or form - I prefer the difficulty to come in the form of a 60–75-mile event with a mix of pretty much any sort of acceptable off-road sections - minus huge drop-offs or stuff that is only suited for a full suspension mountain bike. I rather have the climb to mileage ratio stay 1,000 feet climbing per 10 miles of road or under if possible. I’d rather not have deep creek or river crossings - but it’s not a deal breaker. Crazy mud roads, not a fan of it, and hopefully it can be avoided. Nice things to have a low cost/no cost entry fee’s - I don’t mind self-supported rides and would actually prefer that at times.
On the opposite end of the spectrum, I do like the hubbub and community aspect of certain events. I’d like to do the Patagonia 100 in Arizona at the end of next year - it’s a multi-day event and the race day event seems to be an excuse to get out there, socialize and ride bikes in the dessert. Again, for me - the novelty of the event draws my interest as we as discovering some new roads.
I guess it just kind of depends - it’s like going to a concert - I might like to see the same band over and over, or I might not be interested, but if it’s in a new venue I’d be more interested.