Cycling is definitely painful and gets worse as you grow older so comfort features are very important. I agree that a recumbant is the most comfy of all. That's a no brainer. The 25 year old 10 speed will never be comfortable no matter what you try. I've got one of those too and love it but can't ride it for very long. My best advise would be, for starters get yourself a good comfortable saddle with SUPPORT. Get yourself adjusted in a more upright position. Get rid of the Aero bars and drop bars and all that racing stuff and set up your bike for long distance, endurance riding. You will be able to go all day this way, just not as far and a little slower. JMHO.