Writing as someone who was in the corporate world for many years, I suggest:
1. Always go with top flight fabrics like wool. Some new wool blends now have some elastic so there is some give - may be nice. They weren't available in my suit days. Good wool fabric drapes very nicely.
2. Back in the days when "Today's Man" was in business, they had suits that came with two pairs of pants - that was great. Once in the office, I took off my jacket for the day, so the pants got a lot of wear. If you go the custom route, look into an extra pair of pants.
3. The same suit and shoes shouldn't be worn every day. Put them in a rotation - they will last longer and you will look better with a slightly different look every day.
4. Make sure the suit fits. I've seen people who have very broad shoulders, buy suits that are wide enough for the shoulders, but they hang straight down, resulting in a body that looks like a refrigerator.
5. Use a mirror - take a look at how you look. So many people out there make you wonder if they owned a mirror and realize how they look.