Jayne, I have had 4 professional makeovers at dressing services catering to trans people and crossdressers. Three of the experiences were wonderful and one was just so-so. I can relate to some of what you wrote--certainly about taking everything off and going back to "male mode" (especially since I am in the closet). Since I very likely will never transition (unless my life were to change quite dramatically--so never say never), I am not worried about "passing," and I knew going in that how a professional makeup artist could make me look would be different than how I would look as a woman on a day-to-day basis if I were to live full-time on my own.
Here's how I see it for myself: The experience of going to a transformation studio is a gift to myself, a chance to be the woman I want to be for a few hours in a safe, accepting, and supportive environment. If I had the opportunity to do it every week (and it wasn't so expensive and I wasn't having to hide it from my wife and save up the $$ to do it and do it on a business trip, etc., etc.) Why? Because for me it has confirmed my feminine identity. The freedom, comfort, and peace that I felt when I first fully dressed at a transformation studio helped me understand that I was trans.
Prior to that first experience about twenty-five years ago I had mostly just worn women's underwear, but I had always dreamnt of being a woman (I mean day dreams and dreaming at night). I had wanted to try on my wife's clothes, but they were too small for me. I had filled my bras with water balloons and baggies full of bird seed, but I'd never worn silicone breast forms before that first transformation. Now I have my own forms, my own wig, my own dresses, skirts, blouses, etc.
I know that some trans people have criticized the transformation "industry" as ripping off trans people and I think there are people out there who do rip off trans people. But, the experiences I had were with wonderful people--two of them post-op transwomen who really helped me understand my own feelings as they talked to me openly about my own feelings as they made me up and, in one case, we went out to dinner. It was like a counseling session. The other 2 were very supportive GG's--the only GG's I'd I've ever talked openly with about my feelings and the only people I've ever been dressed around. So, to me, as a closeted trans person, a transformation service (if it is a good, reputable, and safe one) is well worth it!
Now I realize that being a woman is not about being biologically a woman which means that I don't have to "pass" or even wear women's clothes every day. I know that I am transgender and, for me, having makeovers has helped me realize this. Nancy