If you're not racing for trophies or money then reef away! I'd love to know how many cruising sailors have spent how much money on a slightly larger/smaller sail for such marginal gains. If you have a Farr or a J-boat and you're racing to Mackinac, you should have several different sails for multiple conditions and they should all be in relativly new condition and they should NEVER be roller-furled. But for the vast majority of us it really doesn't matter...or at least it doesn't deserve all the attention and discussion this topic garnishes on a regular basis.
There is sail theory and then there is your own individual boat. I think it is best to apply the theories to your boat and then experiment with different levels of headsail reefing while observing your knotmeter and feeling the helm balance. This will give you a very good idea of the best trim for your boat for a variety of conditions. Leave all the worry and expense of trying to find that perfect sail to the racers, even they don't always get it right...and when they do the wind changes and they have to pick another sail to hoist up.
With multiple sheeting options and million dollar materials and design, a race boat is faced with high speed but very narrow operating ranges for each of it's headsails. Sometimes a 7kt wind speed change requires a different sail and a helmsman has to steer a very narrow 'sweet spot' of just a few degrees. Us cruisers need not really worry about such things like we sometimes do.
A 150% with roller furling capability should about do the trick for most conditions we see...oh, and maybe a hank-on 80-100% if you're really looking to do some brisk weather sailing without the concern of the 150 slapping around or getting away from you. An H33 is a heavier boat with a big headsail (especially if it's a 150) and so a #3 like I mentioned should really reduce drag and get you flying if you are sailing in anything over maybe 12-15kts.
Save all the fuss and put in some comfy cushions, a bimini top, and a wine fridge and cash in your pocket rather than different headsails. And maybe check for a used #3. I have a H27 and have an older 90% from a Catalina that I got for next to nothing that works wonderfully if not perfectly.
