Re: For a family of 4 - Islander 28 vs Catalina 30
The Allmand certainly looks pretty. As you mentioned it - if you do get a chance, have a look at the Pearson 323. If in good condition, they are surprisingly roomy, shallow draft, seakindly motion. I really like the I28, but the P323 feels a lot bigger. Both the I28 and P323 are solid, well-built boats. IMHO, for boats of "a certain age", all other things equal I find the build quality of the Pearson and Islander ages better than Hunter and Catalina. Sadly this is also generally reflected in the price! (Disclaimer: I have a P323, my buddy has an I28).
The bit of advice I would give you is don't put too much weight on the looks. Look at the essential (read expensive) systems - engine, rigging, sail wardrobe, deck and hull integrity etc. If you are like many of us, after you buy your boat you won't have a lot of cash left over, so apart from minor things you'll probably end up living with that deisel with 100K hours which sometimes starts - and that will soon sour the prettiest looks!