If you are using a relatively expensive tailor, Tip Top is best if you know what you are doing (eg Manton). If you are making up something relatively cheap, Tip Top is a reasonable option. It is kind of a hassle to get to.
No fittings are quite suboptimal. I've tried it with Chan and went back to doing fittings. Different cloths perform differently, some may stretch more and others may shrink more. For example, some tailors like to add extra length for linen trousers to compensate for the shortening secondary to the wrinkles. To do that sight unseen is kinda tricky.
He's printed pictures of my friends but I've never made it. Closest I came was when I was escorting a friend down the stairs. Her picture was printed but I was cropped out (only my elbow was included).
In case people are interested, Bill Cunningham just died.
NYTimes: Bill Cunningham, Legendary Times Fashion Photographer, Dies at 87
Have you considered interviewing people from the industry? For example, jefferyd had this great post regarding this fake Brioni.Also, since you are in the SF bay area, perhaps Bea (from April in Paris) might have similar insight into leather goods.