Given your list, as stated, you omit any acknowledgement that all these boat are unequal in sailing ability and original design and construction.
Admittedly, after several decades, present condition is really really important, but, still, they were and are not equal choices.
Speed-wise, under sail, you would put the Hunter 27 and the O'Day well under the others. They also suffered from cut-rate engineering and construction back in the day. OTOH, the S-27 and the Cal 27 would be a lot faster. The Ericson has very good sailing manners, and a far stronger hull-to-deck joint than any other on your list, altho the S2 might come close.
For pure sailing, the Cat 27 would be another good choice, albeit with an upgrade to the later-design rudder From Booth up in BC.
I would also agree with other posters that an outboard on a bracket is awful on a high transom on any boat that big. IIRC, only the E-27 and Sant 27 came with transom cut-outs for a stock outboard, and that makes a big difference. Yes, the old Cat 27 did come with a cutout version, but even back in the 80's it was not a good fit for the modern four-strokes coming into vogue.
BTW, you ought to put the 80's Beneteau First 26 on your list. A couple we know bought one for cruising and it's both fast and comfortable.
Well being very new to sailing we really have no ideal about which boat is better than another. I have been trying to educate myself by reading what I can online, (here and elsewhere)and posting this message
It appears to me that the Ericson 27 and Cal 27 would be the best bets for sure. However, one is a bit rough and one has an outboard. Although the owner of the Ericson did say it was not a great light air sailor.
The Catalina 27 (which I would have thought would not have been a lot different, quality wise from the the Hunter) had to my eyes a rather lot of rot in the bulkheads.
The Santana looked neat to me but again needed a bit of work and had an outboard. The Oday27 had a few things that worried me as well.
The Hunter 27 is very clean, I mean clean everywhere, no signs of leaks (yeah I know there will be some but every boat I have looked at had signs of water damage to bulkheads and the Hunters bulkheads look like new.) the motor was clean, behind the storage cabinets and under settee was clean, the deck seems solid, the sails are like new, has a good dodger, bottom is recent etc, etc.
So , yeah it seems from what I can learn there are better boats than Hunter 27s, but this seems a nice example in our price range so I would like to know what is bad about a Hunter 27,(and yes I know a Pacific Seacraft would be much nicer but I can't find one for under 10k
) Just want to know how bad is a Hunter 27, handling, is it really built so much worse or worse sailing than a Catalina 27 or S2 etc.
So anyway good and bad about a Hunter 27? Is the hull really made of Paper Mache, and do angels lose there wings everytime someone buys one etc. Or are they not bad considering the intended useage and price range?
I'm not stuck on this boat its just seems like its in good shape and we have seen some in horrible shape. (Although we found a C&C27 that I hear is a much nicer class of boat, but I think its more than a bit above our price range). Again thanks for all the replies.