Difficult to answer
Some of your questions for you alone to answer. Now, if you were asking *me* what *I* would do...1. I'd buy reaaaaaly used, not slightly. I bought a '73 C27 cuz that's what I could afford. I've never seen the point in buying a 27' boat that costs $30,000! Just my opinion. 2. The benefit of buying such a used boat is that, if you have a decent savings, you don't have to finance at all.3. Catalinas are great for coastal port hopping. They are not designed for offshore work. The hulls oil-can, the rigging would need to be sturdier, etc etc. If you're talking about sailing from Oceanside to Catalina, no problem! From Key West to Bahamas, should do ok if you choose your weather. From Seattle to Australia, forget about it! So I guess that depends on what your definition of "offshore" is.4. Slow? Well, they're no pigs but it depends again on your definition or expectation of slow. They're not slow to me but I'm no racer. It also depends on the size you get. I'd say the average cruising speed of most of them is somewhere are 6-8 knots.5. I have a standard rig and am very happy with it. Maybe I would just love the tall rig but, IMHO, it probably won't affect your speed soooo much to see a HUGE difference. I mean you're not going to go from 6 knots to 12! That decision would be made for me when I found "my" boat. It just so happens that my boat didn't have it. I guess you can't miss what you've never had! ;-)6. The biggest benefit of Catalinas is that they are still in business & quite successful. You can get all the parts, service, etc from them or through various other after-market companies. We carry quite a bit of Catalina "stuff" too. Their service department is quite good - I've heard very, very few negative comments about them.Good luck with your decision. Catalinas are great boats with a good, solid reputation. You can't go wrong with any of the ones you mentioned. Just go check them all out & find one that calls to you!LaDonna