Sorry if I'm over-simplifying this, but as far as I'm concerned if the 'Well Society want money from people they should make it as flexible as possible to pay.
So it's obvious that the £300 membership would cost £25 per month for a year and the £1000 membership would cost £83.33, but what if I could afford more than £25 per month but not £83.33? Why not charge me £36.11 for three years and give me a Steel Membership immediately, then upgrade me to Amber when my Direct Debit is finished? Obviously that's just a quick (and probably flawed) example, but the point remains. Most members don't care about benefits, prize draws or anything else - the £20-£25 won't be the difference between anyone buying a season ticket or not, plus the 'Well Lotto is up and running - people join the 'Well Society to contribute towards safe-guarding the future of our club and want to put in as much as they can manage if they think it's genuinely going to help.
I also think the annual fee should be mandatory to keep your membership and not be fed back into the club to fund daft benefits - I can only imagine what this seasons highlights DVD will be like!