All that said, I don't think that you need to fear that a 26mm sized Rolex will give you more trouble or spent more time in service/repair than any other (larger) Rolex you have. Plus, 26 mm are still on Rolex's menu, readily available.
Buy what you feel comfortable with - what you like - what fits your style. And if that is a 26mm Rolex, that's the watch for you and I'm sure it's going to be a wonderful one that you will enjoy - don't worry about it failing.
Oh, I agree, I totally believe in buying what you like and what fits your personal style and not worry about what people say is in style or not. I like the oversized watch look on other people but don't really care for it for me. I've sold off a couple of my larger, non-Rolex watches since they just felt too bulky and seemed to overwhelm my other jewelry. So, I do think a 26 mm is in my future. I just can't quite decide if I want to go all the way with a vintage yellow gold presidential or another SS model. It's been fun to look! I'll have pics at some point soon-ish I hope.