Your best reality check would be in my opinion to crew (pay your way if requested as you aren't yet skilled) on deliveries or to help an older couple cruise a bigger boat. You'll soon get a real feel for what design attributes, installations and gear works offshore and what doesn't. I consider most boats sold today in the "big name" crowd to be at best coastal cruisers...which is fine, because that is all that most of them will ever be asked to do. Others are unfit for winds over 30 knots and seas over six feet, which on an ocean-going boat is only at the high end of a good passagemaking day.
Try to race during the week and crew on overnighters...and ask a lot of questions and try to read cruising narratives, particularly by the old folks in the '50s and the '60s (Smeatons, Hiscocks, later Roths) who went out BEFORE SAR, GPS, and marinas everywhere made cruising essentially a bus-stop-style service industry (most of the Caribbean). I'm not being critical, but if you want to go off the beaten path, buy a Land Rover, not a soccer mom's minivan, because the DVD player, adjustable mirrors and fold-away rear seats aren't going to impress the lions.