I think by bilge keel you mean water ballast (or am I wrong). Sail magazine recently (last 3 months) had an article about trailer sailors that you should read. It talks about all the things you are mentioning. If you can''t find the issue let me know and I''ll find it (its down in my basement). As far as an inboard diesel being more reliable than an outboard I would strongly disagree. The new 4 cycle outboards are very reliable, don''t stink like the two cycles (or a diesel for that matter) and are extremely quiet and
fuel efficient. If it needs service, just take it off and bring it in. With diesel you can have
fuel problems etc etc etc..... I just bought a 26 foot boat, but it doesn''t sound like what you are looking for--it has a fixed lead keel etc (Colgate 26--huge cockpit for daysailing, small cabin). Again, Sail magazine in another recent issue I think liked the Catalina 25. I would think this boat might satisfy many of your wishes (except the inboard diesel--which you need to forget about). I would think that one reason trailer sailors would not use an inboard diesel is the excessive weight. Thats why they use water ballast--you dump it when you are going to trailer the boat. One web site you may want to try is www.trailersailor.com
Good luck
Rob ~~~~_/)~~~~