Sorry dohcdelsol but I have to probably concur with these two gentlemen. While I am not as familiar with Chef2sail, I have been reading Bilbo's posts for quite a while and I greatly respect his knowledge and carefult tact in post writing.
Bilbo's post was not negative; not pointing to any other favorite boat, or a different boat of any sort. He also was not slamming the Catalina 22, (HE owns one!

). He was only pointing out the very real fact that a C22 has several design compromises that make it a lesser choice for venturing out of sight of land. I have dearly loved both of my C22's I have owned over the years, and at times I regret I don't still have them. Awesome boats! Stiill, I would not attempt to venture across the Gulf Stream in one, whatever the weather.
To your specific questions, the items that in my opinion that would be required to beef the boat up to survive a bad turn of weather out there, (it happens, even on a small inland lake!) would result in sufficiently cutting up the cabin liner to the point of making much of its comfort go away. You will want to positively tab a few bulkheads to the hull proper, not just to the cabin liner.
The cabin was stripped completely bare, i have no issues doing some cutting, all new marine wiring along with all new LED light fixtures/plumbing/thru hulls will be added along with this, I really like your ideas with the bulkheads. I have lots of fiberglass and a year to do this so time is not too much of an issue
You will want to move the chanplates to these tabbed in bulkheads, not relying solely on the cored deck to sustain the loads. That or you could use turnbackles and some method of extending the load down from the existing chainplate locations to the hull or tabbed in bulkheads. Either way, I see a judicious use of a Sawzall on the cabin liner to implement the bulkhead strengthening project.
Replace the existing compression post and re-design it so it carrries the mast load straight to the keel, not to the cabin liner as currently designed.
Beefier gudgeons need to be considered, as the stock ones can and will easily sheer away in the event of a rudder strike.
I plan on working in room for a spare rudder, pretty long/thin so i doubt space will be an issue. The new rudder will be all stainless pindles upgraded to 3 at 1/2' in diameter along with matching gudgeons
The old windows are suspect, as many have no real coring inside deck mold and the upper cabin liner. One might consider pulling the windows, mixing up some thickened epoxy fairing material and packign the voids between the gaps exposed by removal of the windows. then consider ditching the leak-prone aluminum window frames witha new externally mounted window system.
Multiple redundant bilge pumps, as well as a high capacity manual will be necessary, as has already been posted.
The fixed keel has some nice large areas for bilge pumps, as of now it has two 650's in her, do you suppose a manual plus 2 1200's would suffice?
Lastly, (for this post at least) take a long hard look at your pop-top, its seals, dogging-down hardware, overall condition etc... You dont need a large leak, (or even a missing pop-top or slider) to sink the boat. Others have already talked about the need for a higher bridgedeck to keep boarding water from coming into the cabin, so I will not belabor that point.
The pop top (along with forward hatch) will all have to be resealed along with all new teak. Would you go catalina direct for the weather stripping or use something that you can get at west marine/defender/etc? Any tips on making the boards for hatch cover water tight?
Bottom line, the modifications that I would do to a Catalina 22 in order to feel safe with myself and my 18-month-old for the travelling you suggest exceed the value equation in my estimation.
There is ZERO wrong with a Catalina 22 and it is a wonderful boat for its intended use, but as my dad used to say, bring the right tool to the job. If I made an analogy in the automotive world, it would be akin to trying to take a sub-Saharan trek in a Ford Bronco when you are better served with a Unimog or similar expeditionary vehicle. Each vehicle fits its own application...
When the only tool in your bag is a hammer every job looks like a nail
That Ford bronco with Portal axles and a cummins 6bt engine swap might make that unimog look like a yugo in the snow.