Daffy's on Broadway in the Financial District has two interesting sports coats. I would have picked one or both of them up, but just couldn't justify it to myself.
1 Pal Zileri Cashmere Blazer 42L $399 discounted by 20 or 30% so closer to $300
1 Caruso 50/50 Cashmere Silk Blazer 40R $349 discounted by 20 or 30% so closer to $275
To add, I'd say pick collars that are slightly larger than the minuscule trend that has kind of taken hold. The Italian makers such as Borrelli should make something along those lines. If you do go MTM or custom, I think they will also be able to use a stiffer the interlining on the collar band, which should help too. Carl from CEGO would definitely be your best resource.
I understand you are noob, but this type of question really should be relegated to the question thread. You have pictures of stylistically very different grey suits so there would hardly be one answer to your question. Grey and Navy being staple colors there really isn't anywhere where you can't find a grey suit. Now if you are asking for high quality suits then please see below. Do a little searching, a little reading and then fine tune your question to reflect...