We found ourselves in a similar position about 3 years ago.
There are, of course, pluses and minuses going either
route (purchasing
offshore boat now and
living aboard vs.
purchasing a coaster and upgrading to a second boat later). Some thoughts with the latter
route, as that is what I have experience with.
There are significant costs with trading up including
taxes on the extra
purchase, paying relocation
fees twice, the risk of getting caught maintaining two boats, or, taking a loss on the first boat to make a quick
sale.
We made considerable needed
repairs missed on the
survey and some upgrades to our first boat, but always felt held back because we knew that we would be switching up, meaning that any
money we put into our coastal boat we would never see again. Now that we have our Pretorien, we feel rushed outfitting it, meaning we end up paying to have professional assistance (I've then had to go and redo some of their
work that was sub par).
Had we started with the Pretorien, we would have taken on 1 major
project and 2-3 minor projects/year. We would also have been able to do those jobs when it made the most sense during routine maintenance/winter storage, instead of us being forced to pay for an otherwise unneccessary haul and
mast drop during the summer and thus lose a few extra weeks of sailing time for (hasty) refitting purposes. We would also have much more experience with the boat's quirks and how it likes to be sailed in a variety of wind/waves
Some pluses to this approach include that our first boat was smaller and thus 1/4 the
purchase price and about 1/2 the annual haul/store/lauch/dock
fees for the past 3 years (although this would not apply to the OP's circumstances). We were moving up from
dinghy sailing, and a 28' boat was a nice stepping stone. Getting into keelboat sailing on the
cheap also allowed us to assess whether that style of boat satisfied our needs and we ultimately decided to go with something (relatively) more modern.
When we compared with similar era Catalinas (the 34 and 36 mki) the Catalinas felt like they would be more comfortable entertaining. They felt like a condo dropped into the
interior, whereas the Pretorien always felt like you were on a boat. That being said, we've found the Pretorien cozy, but never cramped and everything is built full human sized, so, idk why people would recommend a boat optimized for living aboard knowing that long-term goals look farther afield. Sure, the
cockpit is smaller, but not small for 1 person, their dog, and a few visitors. It's annoying to have to step over the brigedeck every time you enter/exit, and a score of similar small sacrifices for seaworthiness, but, if one's going to have to learn to live with those things later, and one is considering similar priced vessels, I don't really see the argument for an interim
liveaboard, but there likely are a few good ones.
I have yet to take the Pretorien into a chop or any serious
weather with a swell, so I can't speak to it being uncomfortable. Most opinions that I've read feel that it is seakindly, but I appreciate hearing from people who have different experiences. I wouldn't really consider it hard-bilged though. To my eye, the station lines actually start like a more traditional vessel with a deep vee, and only later, almost 2 feet below the waterline, is this truncated by a second turn to a flatter bottom to improve performance over its predecessors.
Just my thoughts,