For a race that I have to travel to, stay overnight, gas etc, the entry fee is really a minor concern. These days I'm more looking for fun, different, challenging, interesting races, and yeah, I'll pay a premium for that.
Example: I haven't done Rouge Roubaix in Louisiana but they have a high entry fee and I'd pay it without blinking. OTOH, I'm not likely to drive/stay overnight and pay $30 for a 50 minute criterium, anywhere.