Steps,
TLW gave you some great words of wisdom.....If, in leaving your boat, you are compelled to look back over your shoulder just one more time to see her sitting there in all her glory - that boat is surely for you.
I know you are looking for Pro's and Con's. I'm not going to give you a professionals point of view, but I will give you some deeper reasons than "I love my boat". But just for the record "I love my boat".
I remember seeing one of the first advertisements for the ODay 28. They pushed it as great small/big boat for those sailors who want to downside. Small, but still big. This is a very accurate assetment of the boat. It is a very big, small boat, or a very samll big boat.
It might be interesting for you to know I moved up to this ODay 28 from a Catalina 27. It is amazing the difference in the two boats. THe 28 ODay is much bigger. PS: your 272 and my Catalina 27 are very similiar in overall size, both width and length.
Why the ODay 28...
1) Wide, actually very wide side decks. THis isn't a cute comment. Once you have had a boat with wide side decks, you will not go back to anything less.
2) Wide cockpit coamings. Very secure for footing. Wonderful for moving forward, especially going around a dodger. Both my 28 ODay and my 27 Catalina have dodger. Getting around the Catalina's dodger to go forward is a balancing act. On the ODay I can walk, with a cup of coffee, around the dodger.
3) The ODay's have a crowned seat for the helm. Sounds like a small detail, but put a dodger in front of you and it is not a small matter.
4) The cabin is enormous. It has opposing settees, which is a bit boring, but highly useable. Both settee are long and comfortable for sleeping, and you don't have to "convert" a dinette into a berth (not that is anything wrong with that). Just easier to use the settee.
5) The quarter berth is seperated from the settee by a small, but very usable cabinet. Gives the person in the quarter berth some privacy, and they don't have to sleep with their head in the other guys feet.
6) Big boat rig. Mast set on the keel.
7) Small head. That's right, that's a benefit. If I can go to the bathroom successfully, the head is big enough. I bought a boat to spend time sailing on, not go to the bathroom on. I'm a simple man.
8) The design of the outside and the inside are "current" even though they are 25+ years old. Modern, but not artizee.
9) O"Days clean up and shine like a new boat. People can not believe my boat is 25+ years old.
Hope this helps.
PS I do not know noaker. I'm located on Lake Michigan, he is in Conn, but wow. He updated it to get it ready for his retirement. New furler, genoa, all the awnings, the instruments look like a 747's, and the much desired swim platform ( don't take that lightly. Sign me up!!!!!