Welcome to the forum.

All your equipment concerns mean nothing at the moment. My 7-year-old just did a 25 mile pre-Thanksgiving "turkey ride" in street clothes on a kids bike. He wasn't last. Keep the perspective of having fun and just riding. Improvement will come whether you have electronics or fancy gear or not. The heart and legs are very trainable after 50.

I would invest in safety and cold weather gear to ride through the dark and winter if you want to get to 50 miles in 6 months. At your likely speed, 50 miles is about a 4-hour ride.

Nothing wrong with being scared of going 30mph. Nothing good can come of going faster than you are comfortable, except shaving a couple of seconds off your loop.