The gloss is produced by two things:
1) the absence of swirls and other paint defects,
2) the repeated application of a lubricated substance over a long period of time.
Frequent washing and waxing can do more harm than good; each time you take pad or cloth to paint you are creating the opportunity to introduce swirls. Proper technique is FAR more important than frequency or regimen followed.
What I did, and it worked, was this.
During the first year of addiction, I addressed the swirl and blemish issue maybe 4 times. During each session I started with a cutting pad strong polish (#83), moved to IP, then to FP. I then used #7 and followed with a wax or sealant (it didn't matter which one). I then waxed the car about every two weeks.
The second year, I addressed swirls in the spring, and again in the winter. During the mid-season I found that the lowly cleaner waxes are FANTASTIC for controlling swirl buildup with multiple washes. I waxed the car about every two weeks.
For the next couple years, I've concentrated on preventing swirl buildup and I've embraced the regular use of mild cleaner waxes rather then the pure waxes. I've probably waxed my car close to a hundred times in the last 4 years. I use #7 a lot, and I use a lot of products that are one step below "purist"; I use a lot of #20, new Gold Class, NXT, stuff like that.
I've addressed the swirl issue once in the last two years, about a month ago. The other day someone (a detailing professional for 25 years) mentioned that my paint looked like glass, and asked if it was a repaint (it's not, and it's a '97). What's happened over the last 4 years is that my wash and wax techniques have improved almost exponentially. I use between 6 and 10 applicators during a wax session. They're cheap, and you can wash them. Why not change them frequently? I use between 4 and 6 wash mitts; same thing. Same with drying towels. Why reuse a wash mitt when you can buy 3 or 4 more, and wash them out all at once at the end of a session? The only extra cost is the initial investment, and I think we all know that detailing tools are worth more than money; you can't dry your car or apply wax with a MAC card, after all.
Technique first, frequency second. Over a 3 to 4 month period, without question I'd hit the imperfections first, then use proper technique and a good cleaner wax every week or two, rather than repeated intense sessions.
This is what it looks like after using a cleaner wax called Ultra Car Care Super Finish; the car isn't just waxed, it's the same day but after about a hundred mile drive:
Tom