Nanook,
I understand your confusion, but after reviewing the information on their website, here is the difference:
For the $99 membership level, you pay for airport lounge entry as you go, at a rate of $21 per visit.
For the $295 membership level, you pay this one-time annual fee and get UNLIMITED access to the airport lounges. So, you have to visit the lounges 10 times in a year to make the unlimited use membership worthwhile.
The $21 "GUEST" fee is just that...for when you invite a guest to come along. It does not apply to you the membership holder if you have the $295 level.
I hope this clears things up. At least that's how I understood their website information.