Hello Bob, welcome to sailnet!
These questions are very difficult to answer, especially with 3 very distinct vessels of varying age, where critical details of condition are unknown to us.
For example, the Pearson will be 30 years old vs. the Hunter @ 16 years old. However, does the Pearson have new/newer sails, Rigging
, updated electronics, new engine, vs. 16 year old sails, electronics and high engine hours on the Hunter?
My Sabre is 27 years old, but the Sails, Dodger, Bimini, Interior Cushions, Rigging
, electronics, lights
, ground tackle
, etc etc..are all 6 years old or younger.
It sounds like both the Hunter and the IP will consume your budget, so the question would be: are they ready to go sailing without futher investment? Advice you often hear here is to reserve 20% of your budget for upgrades and " stuff" on an older boat.
Was there any evidence of leaks on these vessels? Bulkheads sound? Chainplate attachments?
The other thing that I'll suggest is that while 5 year plans are nice to have, understand that plans more often than not have a way of changing through external circumstances and events. So, buying the boat that you and your family will use and enjoy for the 5 years directly in front of you makes the most sense to me. 5 years from now you may have an entirely different 5 year plan. In 5 years, you may have a son in college and another close behind.
With regards to Safety, I think any of those vessels, if sound, should make the trips you mentioned.
Keeping in mind, that safety is often as much, if not more, about the skill of the captain and the decisions made regarding, timing, crew, weather, schedules, etc etc as the vessel itself.
If done properly, the cabin top sheeting on the pearson shouldn't be an issue. You can always get someone to look at the installation for you. In sailing characteristics and construction there's a huge difference between a Hunter and an Island packet. Condition unknown, all things equal, I think the pearson would provide the solidness of the IP with more speed. I'm not advocating for one vessel over the other. I think only you can evaluate the condition of each vessel as it fits your current needs and budget.