Hi Steve, and welcome.
You'll get lots of advice from the guys around here. And if you read through the various areas of the Forums you'll encounter lots of young guys who dealt with a similar situation. So it's not all that unusual. And then there are a fair number of others who are "BBC" (Bald By Choice) simply because they prefer the look or the simplicity.
Your post really says it all. Hair loss is an increasing burden for you. It's taking way too much mental energy to "maintain" the appearance. So it seems to come down to how to transition from your current hairstyle to a new "hairless-style."
You can gradually shorten it (a bit every week or two) like using the #3 guard on the clippers, then the #2, etc. or do away with it all and go directly to #0 or "no guard" or "shaved head." Once you get to the #0 or "no guard" there's really no visible difference between those and shaved, but the feeling you'll get with a smoothly shaved head is sensational.
Everyone's story is different - but the recurring themes are "I should have done this much sooner" and "I have much greater confidence now" and so on. Reactions from parents seem to be the most uncertain. In general, most reactions from friends and co-workers are positive - or non-existent.
If you do go sly, commit to it for 30 days. Those 30 days will help you establish trimming or shaving as part of your daily routine. It will help your scalp toughen a bit. And it will give yourself and others time to adjust to the new look. I found after about a week that I was totally hooked and will not go back to dealing with hair.
But what really matters, is how you feel. It's your head and your life. Take control. If you go sly you will find a sense of freedom you couldn't have imagined. No more worries about hair positioning, dealing with hats, wind, and all.
So take a look around. Ask questions. Tell more about your concerns. The guys here are awesome, encouraging, well-informed, experienced with these issues, supportive, and - at times - quite humorous.