I like many of the features of the modern cruiser. Longer waterline = higher hull speed. fin keel and spade rudder = less resistance and great turning. Flat bottom = more stable and I believe less resistance (not totally sure on that one). Wide stern = living space (nice when you actually live on the boat verse just spending a few days/months on it).
Some of those features make it theorectially faster. However, when I did the race across the gulf, there was a bluewater boat that kept stride for stride with me most of the way. It was a Tayana 37' like this one (
http://www.sailingtexas.com/stayana37a.html). It had a rating of 213 to my 150. The conditions that race were a little rough with winds starting at 28 knots true, down from 35 the night before and blowing the same direction for days. The waves at start were reported choppy 9-11 and seemed at least that. So obviously, my boat was not that much faster then theirs in those conditions...and yes, I do believe the sailtrim was right as I did beat a 54' C&C with an very experienced racer as captain.
So I wonder how the Tayana 37' would have faired with me in light winds.
I own a Ty37
If properly rated a Tayana 37 should have a rating of ~174PHRF plus if well faired, and with 'good' sails, and 'proper/corrected' keel leading edge shape will probably be in the range of an honest 165-168 PHRF. A properly set up Ty37 will have no difficulty in light conditions but as with all fullkeelers you dont want to get into a tacking duel or in any other situation that depends on 'acceleration'. The Ty37 is generally 'overcanvassed' (100% SA ~850 sq.ft; but normally sailed @ `1100+ sq. ft.) so under normal seastate conditions a Ty37 is normally reefed early but will remain quite stable (and comfortable) well into F8-9+ conditions.
"in the classic boats, does the weather helm increase as the boat heals more?"
Most of Bob Perry's 'double enders' (Tayana, Baba, Tashiba, Valiant, etc. etc.) have quite symmetric hull forms so that if well trimmed can sail almost over to their beam ends ... and with little change in helm. Being relatively narrow beamed, there is large intitial tenderness but they harden up well at ~20deg. For passagemaking they tend to 'slow roll' (maybe a bit 'top heavy') that tends NOT to tire out the crew as would a lightweight with a 'fast roll period'. The bow entry angle on a Ty37 is quite high/large so that when beating, the larger the waves/chop the less ability to point, unlike a boat with a 'fine bow' that points much better in all conditions (but you have to be out of your mind to always be pointing on long distance passages).
Too bad that Pacific Seacraft went belly-up as the 'evolution' of quality passagemakers in the 'under 40 ft. range' was about to be 'stunningly optimized' by the Bob Perry design of the new PS38.5 - a design that seemed to be latest evolution and refinement of such sized 'deep water boats'. When asked Perry stated that the PS38.5 would be the 'todays/modern' version of the Ty37, Baba40, Valiant40 and all the other 'derivitives' that followed. The fact is that more of these Perry-boats have circumnavigated than by any other designer.
I power-puke less in a slow rolling boat.
Symmetric hulls are easier on windvanes/autopilots
Once I get to hull speed I can reef.
A deep in the water boat by design generally can carry VASTLY more stores and still sail on her design waterline. A lightweight boat fully loaded with stores will be much deeper in the water and may become very 'cranky'.
If I were buying new Id opt for sloop @ 7/8ths rig with solent stay, BIG mainsail but 4 reef positions, less than 40ft. so I can still be able to manhandle the largest sail on a pitching deck if needed, moderately fine bow, split underbody, 'semi-balanced' rudder ON skeg, retractable bowsprit w/ roll-gen for spinnaker, ALL primary sail controls back to the helm (not cockpit) including end-boom sheeting, drop down swim-platform (flush when sailing), double backstay, NO 'staysail', windshield instead of dodger (maybe a soft easily removable top).... and importantly, alternative easy access stowage places so one doesnt need all that 'crap on de back' .... a 'clean' boat for minimal 'windage' - no ugly 'oil derricks' or 'roll bars' on the back, no aft rail clutter, etc.