Welcome to BYC!
You will get as many answers as there are people who answer your post, LOL. Since you do not already have birds, have you thought about checking out what others around you are doing? How does it work for them? Do they actually like it and if not - what would they do to change it? How does it protect their birds? How is it to clean out the coop, the run, the next boxes?
How much time do you have to clean daily/weekly/monthly/yearly? What do you want built in for your feeding/watering/nesting?
I am a fan of having less work and birds on the ground - so even coops here sit on the ground w/o any flooring and we use a variety of materials for the bedding (DLM). We get hurricanes, freezing rain, snow/ice and a lot of wind. We have had drainage issues a few times - we've moved the coops (portable at one time, not so much any more); we've dug trenches to direct water. We have had plans to install gutters on various buildings and haven't yet. We have not put in actual french drains - just didn't get to that type of project yet and have found that during storms, just redirecting the water has worked for us. We are also on VERY sandy soil and I love using the DLM method to bring it around to better soil. It mostly drains well - so even when it's gotten wet, we usually don't have pooled water for any amount of time and as each coop/run builds up the DLM we have fewer such issues.
We don't bed the tractors - even during storms or cold. We do move them to fresh ground regularly. Right now, we've had rain almost every day for the past week and the rest of the Holidays promise more to come. It's not coming down in deluges but instead misting & sprinkling alternating with periods of harder rains. We did end up with some pooled water in our drive way, but all the tractors and the coops are doing OK.
I do not know what type of weather you actually get there, though I have been up to Holmes county many times in the past 10 years even during the winter. That open front combined with a run might work out great - only putting up hardware cloth and being prepared to line it with plastic or wood panels during the wettest/snowiest times. I think I'd put a roof on an open air run and put in either cement or hardware cloth aprons below around the building your coop is attached to as well and repair the roof you have. Your chickens will be healthy and happy. My 2 cents worth.
Happy Holidays!!