Jeanneau Sun Odyssey 32.2 ?

[boatman61]

Its a Bene 323, not a Wharram catamaran..
Jerry cans strapped to the side decks are fine poodling round the Med but for me the less deck clutter the better on ocean passages, even on so called milk runs the S-hit can hit the fan..
Beside's, where'll I strap my canoe with them in the way..

[double u]

...even on the Elan 410 we hat 4 x 12l "Jerry"-cans tied securely in the cockpit, to take into the raft in an emergency. Tied to 2 eybolts they would have stayed in place with the boat upside down (BTW: LadyCaptins verious threads are the entertainment of the day...endless ruminations & "statements-of-requirements" of people used to a motor home....o tempora, o mores...!)

[El Pinguino]

Now that we seem to have the skeg v. spade issue sorted have you ever considered a Westerly?
Maybe a 33 foot Westerly Discus such as sailed by Bob Shepton further north than any other yacht.
https://vimeo.com/152958661
https://sailboat.guide/westerly/discus-33
If you compare the plan view of the Discus with that of the Contessa you can see that not only is she 0.5 metres beamier but also carries that beam for more of her length so much much more roomier. Note also so she is 28.5 ft LWL
https://sailboat.guide/contessa-32

I'd go for the fin/aft cockpit version

If you want a little bigger there is the Conway
https://photos.inautia.com/barcosOca...152484569x.jpg

Or maybe even the Corsair
https://westerly.apolloduck.com/boats/westerly/corsair

Some points. Forget bring the dog aboard over the stern - with the dinghy beam on to any slop, pitching movement amplified etc. Bring him aboard amidships - this may involve a modification - fitting a new wider 'gate' amidships maybe?

Old money pits? All boats are money pits - just avoid one that wants all your savings on day one. If generaly sound look for one with a reasonably new engine such as a Delta, decent sails, and fairly new standing rigging. Then you may go a good ten years before she next wants to really get into your bank account.

Skeg v Spade? There are good spades and dodgy skegs and v/v.
I've never heard of either type being a problem on a Westerly.