Honestly, if your main goal is just to look presentable for rich clients, then just stick to JAB or maybe Brooks Brothers if you want to upgrade a little bit. Get it tailored and you will look fine. To your questions:
1. Pleated, yes.
2. Cuffed or not, doesn't really matter. Some people say cuffs always with pleats, but no one is going to really care.
3. Don't know what you mean by checkered stripe. If you mean a glen check, it's a little risky for the conservative...