FreedomYachts.org

I’m considering moving up from my F30 to a larger Freedom Cat Ketch and looking for advice from those who have owned or sailed them. Forgetting about current condition of the boat or price, which would you consider the better boat for cruising: the F44 or the F39 Express? I’d like to compare sailing ability, livability at sea and at anchor, serviceability, build characteristics, or other. Hoping to generate some controversial opinions and debate .

I would kinda like to hear some thoughts on this. Just curious.

I've never seen an F44, or a 39 Express, but looked at both the F40 and the 39PH – which is a schooner, not a cat ketch.
The PH had a pilot house/saloon, which would have been great for sitting at anchor in a beautiful place, or sailing in inclement weather. Fast, but with a deep fin keel.
The F40 (aft cockpit) was a more sea-kindly type, shallower draught (with c/b raised) and loads of deckspace, for dinghy or deck chairs or playing quoits. A big sprayhood kept the cockpit fairly dry.
Two things about an F44; bigger size means higher mooring fees if you don't anchor, and bigger anchor if you do. Also, in some jurisdictions, being over 12metres in length brings extra regulation about safety and other equipment needed to comply with SOLAS regulations.
Were I to be sailing as fast as Ron Holland's hull will go, I'd want the Pilot House schooner; if I was cruising open waters comfortably with a usual crew of two, and occasional visitors, I'd go for an F40. I once met a couple in their late 70s who had just sailed theirs to Svalbard (well into Arctic waters), by themselves, and looked as fresh as daisies on their return.
In fact, we decided even a forty-footer was too big for the sailing we wanted to do, and got an F35 (33 in the US) cat-ketch, perfect for Scandinavian coastal waters.