Ahoy Ducati,
My personal preference would be the Island Packet, a "Better Boat"! You seem to have figured out which are "Good Boats" and "Better Boats", values for these boats reflect the differences. Having said that, you may find a "Good Boat" in excellent conditon, and a "Better Boat" that's not in excellent condition, and the prices of these boats comparable! If you and your wife have an opportunity to look at some sailboats, we all like to know what you think about them, and why?
The reason I prefer Island Packet is because they were designed for crusing, there are plenty of them out there, and my feeling if you going to invest and travel on a sailing yacht, why not go with one of the "Better" boats. Your budget enables you to purchase a "Better Boat".
Years ago I went through the same process you and your wife are going through! I was in the market for a "Good" 28'-30' coastal crusing sailboat. At that time I looked at Beneteaus, Catalinas, Hunters, and Pearsons, because I really didn't know much about any other brands. Finally settled on a 86' Pearson 28. Thought it was by far the best of the sailboats I had been looking at. Looking back I didn't bother to look at Compacs, Island Packets, and others. It may have been because of my budget! However, I purchased a new Pearson, about $50,000, then spent between $15,000-$20,000 outfitting her. Had I been wiser at that time, or perhaps had some input from others, I should have purchased a "Better" older boat. Then, I'm certain I'd have purchased a lot more boat for the same money.
The experience I've gained in buying and selling boats prompted me to buy the 89' Compac 19/3 we have now. We live 115 miles from the coast of North Carolina and that's why we are trailer sailers. Compac makes one of the "Better" trailerable yachts! They also make a 35' Compac, which isn't the length you are interested in. However, there's one for sale in California, i.e.:
I'm not particularly fond of a dark hull, but it's a solid good looking boat. It's a 2006 model, with an asking price of $140,000.
http://www.yachtworld.com/boats/2006/Com-pac-35-1518699/San-Diego/CA/United-States
There are so many boats out there it's definitely a buyers market! Your have an opportunity to make a rediculous offer on a boat, and who knows the seller may just sell you the boat! That's my 2 cents worth! Good luck!
David