Great advice above. And don't be afraid of the older bike. I have a $5000 custom, full carbon, SRAM Red, Race bike...Funny thing is, I still like riding my 25 year old Schwinn for "around town <20 mile rides".
Invest in a proper fit at your local bike shop. Make sure your seat is not too high. This can put extra pressure on the family jewels as well.
As Admin said, those two investments are gold. If you are not willing to go with clip in shoes, just make sure you ride with a STIFF soled shoe.
Keep the shiny side up. You will be doing a half-century before you know it.