I don't think the outcome of these medical procedures will improve over time, unless there's a significant enough technological advancement within the next few decades. Skin will still scar, the body will try to heal the surgical wounds despite attempts to prevent it (in the case of a vaginoplasty), and the SRS results will still look like absolute shit to anyone with functioning eyes regardless of the surgeon's skill. Nothing but a magic fairy wand will make the fake genitals look like real genitals.
The first recorded vaginoplasty was supposedly done in 1931 on Rudolph "Dora" Richter, with Einar "Lili" Wegener following after with a penectomy and an ovarian and uterine transplant. The first penectomy was supposedly done in the early 1950s. Now, SRS didn't become more popular until more recently, especially with certain doctors who made it into their life's work (see: Dr. Suporn). Even though SRS has been done for decades, there's relatively little progress in the way of the end results, aside from lighter/less heavy scarring in some cases. After some pushback, documenting failed SRS is becoming more common, with criticism against SRS doctors being more pronounced - this was unthinkable several years ago, as dissidents would be shouted down by their peers.
All in all, it's going to be interesting in the next few years when more people share their experiences and efforts to suppress peoples' negative experiences ultimately fail.