In retrospect those first rounds were terrible; the wealth of good information available today (and the 'real talk' presentation of it here) makes things easier by orders of magnitude.
I was 18 years old living in my first apartment. I converted my kitchen table into a reloading bench. Made some 30-06 with IMR 4350 using an RCBS Barbie dream house kit of the day. My boss at the time was a reloader, but at 18 it's awkward asking your boss to mentor you on the weekends etc. I was pretty much on my own.
I remember being terrified that I was going to blow my gun or myself up, but somehow it worked. Not any better accuracy than factory ammo, but it worked. Perhaps the most important thing was just getting started.
I also remember having a sportsman's warehouse (with a reloading section) two blocks from my apartment, and wanting to shoot every combination possible. I must have put 1000 rounds down that crappy factory tube the first month LOL!
Edit:
To answer your questions...
How long before it became second nature? Not long, however I wasn't doing it "intelligently" until several years later; competitive shooting was a massive eye-opener in terms of reloading practices. I think most of us are on a never ending quest for better tooling, and better methods.
And if you think you're invested now, God help you 10-15 years from now. I heard someone at a match say this the other day, and I think it's true for a lot of us "I got to thinking the other day, I could probably pay cash for a truck with everything I have invested in this shit....like a brand new 1-ton diesel"
