Hi Amy K-- so you have a boyfriend who sews for you, and you are interested in sewing for yourself as well? Or you are wanting to know what's involved in his sewing for you? Either way, the questions you ask are good ones to consider before jumping into a sewing project.
I guess I do sew for a living, in a sense, as Angie asked; I sell sewing machines and teach sewing classes. But I still feel like the sewing I do is mainly for myself and for my own pleasure.
Sewing takes a lot of time. There are patterns out there that say "1 hour" or "2 hours," but I find nothing goes together that quickly until I've tested the pattern and altered it to fit me. And I second everything Amy says above. My process, once I find a pattern and fabric I want to make up, is to test the pattern by making it in a similar fabric to my "final" fabric, seeing how it turns out and whether I do want to continue with the pattern or not. And I make alterations to the pattern, based on my test. These changes are first for fit and often also for style (I want to change the sleeve or where the waist hits or something like that).
How to decide what to sew and what to buy: I sew 1) what I can (i.e., what's within my capabilities, 2) what I want to spend my time sewing, and 3) what I can't buy more easily or readily. So, for example, I don't sew my own jeans, although I'm sure I could if I put my mind to it; per #3, I can find them more readily in the store. I know some women who just can't get the fit they want in jeans, so they make theirs. I love to sew knit t-shirts in various styles that I like to wear, because knits are easy for me to fit and sew, and I can get unique tops that suit my wardrobe and that I would never find in the store. I like to sew clothes that are relatively unstructured (hence, easy to fit, less time involved in the pattern-testing) and that mimic pieces I could not afford to buy. While it's true that you don't save money by making your clothes, in the way we used to do while I was growing up, I find that there's a point at which you can save money by sewing; last year I made a coat inspired by one I saw online for around $2,000.
Like Amy, I love the creative process of sewing. I learned to sew from my mother, and I've been sewing since I was a teenager, off and on. But there's a fair amount of what I sew that does not see the light of day outside my sewing room. Much of the unworn sewing is test garments, but there are a lot of things that just don't come out the way I envisioned them. Sometimes I adjust my desires to fit what I ended up with; sometimes I turn "mistakes" into "design opportunities." And sometimes I just end up tossing a garment in the donate pile and chalking it up to the product of a day spent doing what I love to do.