Hi - I'd want to see the technical specs for the Winegard antenna before I purchased. I looked at the Winegard site and all they give you are the installation manual and a claim of a 60 mile range.
I was going to point to the excellent technical info on the Antennas Direct site, but they don't give you a lot for the CS4. Compare to the DB4e
https://www.antennasdirect.com/cmss_...s/DB4E-TDS.pdf which has quite a lot more detailed technical data. The CS4 says it has 12.2 dBi gain, but it also says it works well with widely spaced towers. That's not what you have - you have two groups of stations at nearly 180 degrees from each other. The gain pattern of the DB4e is certainly broad enough to cover the whole group of stations from Orlando, and you might pick up a station or two on the back side. It is possible to remove the reflector of the DB4e and pick up signals from both the front and the back, but at somewhat reduced sensitivity in the forward direction. You can easily drill out the rivets that hold the screen in place and try it, and then put the screen back with some screws and nuts if you want to return to the original configuration.
Regarding your metal roof, I recall that we have covered that here before. You could search old posts. I know that the metal roof will form a ground plane below the antenna, but I don't recall how much vertical clearance you need to avoid any negative effects. I'd guess you'd want 5-6' feet or so.
Eave mounts are sold commercially, but they aren't meant for easy removal in advance of a hurricane. I'd think you'd want something like a long mast that attaches to the peak of your roof, and which can be tipped down if a storm threatens. Telescoping masts are available commercially. If you look online, there are a few examples of hinged towers that pivot to lower the antenna to the ground - that might give you some ideas.
Another comment - the Eagle-Aspen is cheap enough that in your position I would buy one and test out my reception in both directions. You can get a 10.5' chain link top rail at the home center for a mast, and rig that to hold the antenna on your roof, with a long RG-6 cable. Point it at Orlando, then point it at West Palm Beach, and see what you get. Try it without the reflector and see if you get stations from both cities.