As long as you have bought something that you can wear, that's the main thing. I have bought things that saw almost no wear - they were not worth the time or money, but were part of an ongoing educational experience to discover what I liked in clothing, shoes, etc. A good piece of advice I have received (and hold to be true) is to acquire things slowly and thoughtfully (but not too much thinking as your time should be spent on other things). The best thing is when you have a piece of clothing that suits your needs for many years and one that you don't have to upgrade/replace because it feels cheap (or not as well made as you would like). That being said, there is no such thing as "investment" in clothes or shoes.
Myself, I go for jackets that are soft, comfortable and light. I live in Melbourne where we have both cold and wet (but not snow), and very hot. I think dressing to suit the environment you live in (colours, fabrics, function) is important. I think fit and construction are vitally important. I am surprised sometimes at how badly some "tailor made clothing" can be, and sometimes ready-to-wear can be well-fitted and better constructed, even better priced. A good example would be stuff from Ring Jacket, Boglioli, Boggi Milano. I've had jackets from such brands that are better than certain HK tailors, at a better price as well.
Your last photo shows only part of the jacket (I am guilty of doing the same thing) but there are a few comments I would make. I guess if you wanted more comfortable jackets, you would ask for a lighter, less padded construction with softer canvas. Think about a softer shoulder, but I would probably not ask for a spalla sleeve head as I have only seen good examples from Chan or Yao. I don't see a lapel buttonhole, but maybe you asked for that to be removed. There are issues with your shoulder fit, and I suspect that the shoulders need to be more forward pitched to prevent that amount of wrinkling while holding a neutral, anatomical stance.
I submit four jacket fits to share the aesthetics I like and also for constructive criticism:
Warning: Spoiler! (Click to show)
Edited by iSurg - 11/9/13 at 5:36am
1. ready-to-wear unstructured Boggi Milano cotton jacket, Liverano (fujito) jeans, denim shirt
2. ready-to-wear Al Bazar herringbone blazer (unknown mill fabric)
3. made-to-measure unpadded jacket from Australian company "P Johnson Tailors" (Dugdale worsted, I think)
4. One of my favourites: Orazio Luciano made-to-measure in Loro Piana 3-ply with minimal padding
Granted, I cannot afford most bespoke other than Chan (definitely not any Italian or English bespoke operations), and it will likely remain so until I am personally comfortable to spend at a higher bracket. I still believe that there are options for every price point, but a lot of them require you to visit in-store. Some Italian stores I visited sold very well-made jackets for 300 euro...
I think it might be wise to try other tailors, such as Y William Yu over Simpson. Don't have to order much - maybe an odd jacket and odd trousers. Otherwise, give some ready-to-wear companies a go if you get a chance to visit stores and try on