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Hello and welcome!
It looks like you have access to both the Green Bay stations and the Milwaukee stations. Since these stations are coming from opposite directions, I don't think you'll be able to pick up both cities at the same time. This leaves you with two choices:
1) Just pick one city and set yourself up to concentrate on only those channels. The Green Bay stations are a little closer and easier to pick up, but there appear to be slightly more channel choices coming out of the Milwaukee area.
2) Set yourself up with an antenna rotator or an A/B switch so that you can watch stations out of either market. You just can't do both at the same time.
As to your other questions:
>> Yes, if you are dumping cable TV, you can send your antenna feed into the same distribution system to get the signal to all the rooms of your house. I would recommend installing a mast-mounted pre-amp to make sure your OTA signals overcome the loss caused by the splitter and lengthy coax runs.
>> Yes, you can use a DVR for OTA programming. It doesn't work quite so well if you have an antenna rotator (or A/B switch) and can only have the antenna pointed at one set of stations at a time. There are multiple DVR options out there that can handle OTA programming. Some require a monthly subscription fee and some don't.
>> If you continue to use Charter Cable for internet service, you need to somehow get the cable company's feed connected to the cable modem/gateway appliance in your home. If you are taking over the coax distribution network for your OTA signals, then it means you need to separately run a connection from the cable company's main feed to the location of your cable modem/gateway. If this device is acting as the WiFi access point for your house, then you want to make sure it is located centrally inside the home (so that the WiFi signal does not need to travel far to reach any point in your house).
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