Catamaran Cruising

Simon, It was good to chat on the Monthly Zoom! 
My advice would be to go for it and enjoy it. 
We first "did the Bill" in a 22ft Hirondelle, religiously following the almanac advice. I think the best advice is to stay close! But also to be aware of the southward tide that can easily draw you down to the race if you are not careful. The advice on the return leg to aim for a point well to the north of the Bill (as you will be pushed south as you get closer) is good!. 
Later, in the Catalac 8m, we decided to go south of the Bill to avoid it altogether, and I have a waypoint 5NM south set as being "safe". This does not give any real options for stopping in Portland or Weymouth, but we had a few good passages in good weather from Dartmouth back to the Solent. We usually timed these so the tide was against as we were roughly 5 miles south of the bill, so we could enter the Solent with the tide and get the huge rush up to Cowes. The disadvantage was going for a nap off watch and finding the Bill roughly in the same position when waking 2 hrs later. 
I would also recommend trying some navigation programs to help with planning (and to beat the winter blues!) . Those of your who know me know I love the Neptune Navigation passage planner and I have had it on the boat PC for many years. I just love the fact I can plan passages and it does the tide work - and - uniquely as far as I can tell- It will give you estimated passage times at 1 hr intervals for the day, so you can see the effect of getting the tide right, or wrong. I have no links to Neptune Navigation!.

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