Originally Posted by 79pmooney

You have an 8-speed. More means changing the brifters. Perhaps the wheel if you cannot find a compatible cassette. But if you find that 110/74 BCD crankset, you now have a lot of options, for both now and the distant future. (As a 71 year old, I have witnessed many gear lowering since I was your age.) You will be able to find chainrings for that crankset for a long time. Many, many bikes were built using it. With different bottom bracket spindle lengths, itis incredibly versitile.

A plan that starts cheap and never gets too far out of hand would be to get that 110/74 BCD crankset (there are a lot of used ones out there) and a 28 tooth cassette with whatever small cog you can get. Now the fun starts. Go to an online gear calculator. (There are threads on BF with lots of info on the best, easiest ones.) If your present high gear is good, then an 11 or 12 tooth small ring can be used with a smaller large chainring to get the same high gear. (ii tooth, you'd be looking for a 47 tooth large chainring. Going to a much bigger big cog means the cassette spacing will get much bigger and you will find that your favorite flat ground gears aren't there anymore and the jumps are much bigger. So, play with that calculator, looking for large and small chainrings that give you the low and high gears you want with that cassette - and have as little duplicate gears as possible. You may well find you can get most of those favorites with slightly odd shifting pattern and still have a high gear that suits your needs and a low gear that works for your legs.

And in time, that low gear will no longer be cutting the mustard, so to speak. Brace yourself. Now triple time is coming. You'll need a new bottom bracket, probably derailleur, perhaps a new front shifter (a good, not very expensive option is to keep your brifters and just add a bar-con front shifter. But you already have the crankset, the building block.

Now, that second step is a place where there is room to save bucks. You will know long in advance it is coming. So when that sweet derailleur shows up at a decent price you can grab it. And so on. When you don't need it tomorrow, bargains happen.