Hi tom,
If you use the search function, you will find a bunch of threads about tires, alloy rims, etc. There are a lot of opinions and you'll decide what's right for you. There are a number of us who have successfully gone to 205/70 14s. The wheel wells are narrow and some people have had rubbing issues in the front. The suspension needs to be good, obviously. My local tire store guy mounted just one and we eyeballed it on the ground through the full steering range before I decided to purchase the set that size. (Don't ask for that on a Saturday)
I live in Jacksonville, where, when it rains, it does so with enthusiasm. So I picked a tire for it's wet braking. I have Yokohama Avid A-4s. They were the best in class for wet and the softer compound gives great cornering in the dry too. I won't expect more than 35,000 miles from them, but that is a lot for this car and the performance is worth it.
You can go to tirerack.com and compare lots of makes with road tests and user reviews. Be sure to look at the specs. Note the diameter of the original size tires and look for that in the wider replacement. Also keep in mind that the wider tire might not fit in the trunk.
I think that the factory alloy wheels are 1/2-inch wider than the steel rims so they should help with sidewall roll and traction too.
Ray
'68 280SL 4-spd Coupe