Yer all screwed, most of the boats you have chosen need crew. Which as I can attest are in the main unreliable, costly and often crap.
What you really need is an X-Boat or Solent Sunbeam or an upto date International 14. There you only really need 1 crew who will be as passionate about getting round ChI Harbour in first place.
Or that Wally that you can sail single handed.
I’ve sailed Ultra 30’s, whilst a whole lot of fun, organising crew was a total nightmare and when they went over they were a huge pile of pants to get upright, Ossie will back that up.
Or I’d go for a Figaro or an IMCO 60.
Sheet in.