My .02 cents worth would be to go do some training on a larger boat,something around 35 to 45 feet,especially if you think you might do some liveaboard for a bit.
Boats tend to shrink once you abilities progress,buying a too small boat is a common issue if you get the bug.
Training or chartering will get your bad habits under control quickly at minimal cost.We started with a 25 footer which we grew out of in a couple of months,then to a 34 foot twin screw which in hindsight was a better place to start for us,then to a Defever 44 which was a fantastic boat in which we went all sorts of places,it had enough fuel/water,twins,genny,seagoing ability and living room to live on full time in comfort.
We've now gone the whole hog to a Cheoy Lee 66 LRC which we live on pretty much full time,it possibly too much boat,but what the heck,life is short and she's very easy for two of use to manage,easier than I would have thought before we got her.
As far as boat choices go,production boat are usually easier to resell,and they mostly have know faults.Boat to look at in the slow comfy cruiser range would be the Grand Banks 32 ,36 and 42.Defever 43 and 44 etc.It all depends on how rich and famous you are.