I popped my IM cherry in Bolton, but my first HIM race was The Little Woody the year before. I went through the same thought process. Should TBW be my first long race, it's cheap and it's local. But for me, I didn't want to finish, and it but be s branded IM event, just in case it was a let down, and also having to forever explain the differences. I also did IMW in 2011, and it is an awesome event, and hopefully I'll be back in 2013, something of a buzz on Tenby that I haven't got elsewhere.