Welcome to the 281 club! I have enjoyed ours, and it's a great boat that doesn't take a lot of work. As far as intruments, I put in a navpod that has the original Raymarine TriData (which is good for depth and water temp, but I would not use it for speed), a Standard Horizon GPS (good for speed), and a TackTick wind speed and direction unit (very cool wireless, solar-powered system). I also ran a RayMic up through the navpod so that I would have a Class D VHF speaker and microphone close at hand. While not cheap, this takes the 281 into the 21st century and gives you everything you need. I have not put an autopilot in as we don't do a lot of long distance cruising. Other things that I have done on her that have proved useful and fun are: installing dripless stuffing box, Racor fuel filter system, new stereo with speakers in the cockpit so that you can hear some music while sailing, covered the wheel in leather (fun little project if you like to sew), new bimini with stainless steel frame, new cushions, all new canvas, new lines, and an automatic bilge pump below the engine (Wale Super Sub) that has its own separate thruhull. While this was a lot of work over the past two years, it's made a 16-year-old boat almost like new. I expect to have many years of sailing her, and even though I sometimes wish for a few extra feet, what I have saved in not getting a bigger boat I have been able to use with the upgrades.
I haven't found many problems with the 281. I did replace all the port gaskets since they were leaking, and the lack of an automatic bilge pump is always an issue (but like I said, the Whale super sub with a separate thruhull and circuit solve that problem). It doesn't back very well, and the stock auto furler for the jib is pretty basic. But it sails great, and there is more room than most boats that size. Let me know if you have any specific questions in the future.
