I think I have to agree with Denise on this one . Once you get to a certain point in your sailing experience , that trailer sailor will get old . I have a little daysailor myself and thats just so I can keep sailing right now . Its a temporary measure . I have owned two full keeled boats myself and crewed on I dont know how many others of varying hull designs . It sounds like its time to step away from the trailer and get a beefy bugger with some ballast .
As I said Im a trailer sailor myself right now , however I dont think a day has gone by in the past two years that I havnt been on line shopping for my next cruiser .
Best of luck with it ,
Its hard trying to nap with that bilge pump alarm going off all the time