Re: How high can you point?
Mostly, it comes down to your foils.
If your sails are blown out, improperly trimmed, if your keel is damaged, or foul with growth, you won't point high.
Also, some lifting keel and centerboard boats don't point as high as their fixed-keel cousins.
Boats that sheet to the toe rail will not point as high as boats that sheet inside the rails. The tighter sheeting angle reduces the "stall point" of the foils.
Achieving 90 degree tacks is pretty easy if you have even fair sails and a clean keel. Getting the next 5 or 10 degrees requires knowledge of fine-tuning your sail trim. (Sail twist, halyard tension, jib car placement, traveler position, etc).
In some conditions, (like upwind into a foul current and a chop) you're just not going to point very high and maintain any decent amount of VMG (velocity made good). You'll have to foot off a bit, to build speed to power through the chop.
LOL...oops, I see zzgta has beaten me to it. Heed his advice, he's a winner and I've raced with him.
S/V Old Shoes
1973 Pearson 30 #255