John.. Interesting project!
It seemed to me to be relevant that everyone who has replied says, yes, they have done this but in larger - and hence, heavier boats and it occurred to me to wonder why you would want to do this in a trailer sailor, that is designed to go on a ferry and then enjoyed when you get there ...!
However, having done about half a dozen passages in open water so far this year all of about 50 odd miles each, in strong tides and in heavy shipping in my own Baycruiser 23 'Equinox' - and with more than my fair share of strong winds. I can reassure you I think she is capable.
But .. and I may be wrong, but from the pictures on the tumblr web site - it looks like Cara doesn't have spreaders with additional stays on the mast? You may want to have a chat with Matt about this before you go 'off shore' - he certainly insisted I have them when we discussed my order and the type of sailing I knew I'd end up doing. In fact I thought they were now standard on the 23?
My own observations would be to make sure you can shorten sail quickly and efficiently and are well practised. Both head and main sails and in good time - you probably already know that the BC23 will sail very well, with little heel on double reefed main only. With the foresail tucked away, I find it's usually 'calm' enough to make a brew etc - I take it you have some kind of gimbled cooker, you'll need it!
The AIS/DSC is indispensable - Have your CPA set for at least 5 miles. As others point out, the enemy will be be upon you before you know it. An AIS transponder would be even better but I appreciate few have them on our small boats. Radar reflectors are also an asset - even a reactive radar transmitter? You may want to 'book in and out' with the Coastguard - personal thing, up to you.
In my experience using any kind of paper chart on the BC23 is impossible - maybe that's just me. I use a yeoman chart plotter sport (brilliant! Why have they stopped making them?) in conjunction with a conventional chart plotter. I also have an auto helm. EPIRB for peace of mind?
You'll want sufficient means of keeping batteries topped up for a long passage, some of which will be in the dark.
Re documentation, it may be worth having a chat with your insurance company! The BC23 is a cat C boat not designed for this sort of venture .. I doubt Matt either will publicly condone this although privately he may well agree. We took a Parker 21 across the North Sea - the designer (Bill Parker) agreed it was very possible but couldn't officially say 'yes, fine. Go ahead'
Having said all that .. If you're happy you can do it, go for it!
Andy and Equinox .. Baycruiser23 No. 25