Don't think clipless will help you much unless you ride a TON of hills. And even then, not so much.

Better off getting premium flat pedals -- ergonomic pedals or something like MKS Lambdas. I ride pretty much year-round with North End waterproof trail running shoes -- reasonably stiff, good protection as long as it's not raining buckets (I got clearance-sale Showers Pass rain boots for that) and lasts a really long time when you don't use it for running. Also great as every day shoes. Their only downfall is the insane prices they charge, which I tackle by shopping at their outlet stores during BF.