Yes quite probably. My first thoughts with the antenna would be something with reinforced hardware, due to the storms you likely get being near the Great Lakes. A ST2 Scantenna would not stand up to much of that, and cheap discones are likely to fall apart. These 2 are a start - look at the Omni X from DPD;
DPD Productions - Scanner, Aviation, NOAA, Mobile Radio Antennas for Commercial & Hobbyist Applications
Scanner Antennas | PAR Electronics | Filters for the commercial 2 way market, MATV, FM broadcast, laboratory, marine industry, amateur radio, scanner and short wave listening enthusiasts
If you're further away from the transmitters then a beam is called for - Grove Enterprises sells 'em, as does DPD. But let's start with the simpler solution first.
The next thing to consider would be coax - likely as not a RG6 variety would be right up your alley. You would, of course, need the proper connectors to go to the antenna and scanner - I'm not sure, frankly, who you could ask in your neck of the woods about this - I would check in our
Wisconsin forum (note that anything blue is a link).
Next would be waterproofing. The coax going to the antenna is going to take a pounding - wrapping it in a double layer of electrical tape that is then sealed with a silicone sealant at the jack where the antenna and coax mate is going to be vital. Failure to do this will lead to eventual water leakage into the coax, causing signal loss.
Another thing to keep in mind, as mentioned earlier, is the fact that GRE radios are prone to overloading particularly in the VHF hi band, where your transmissions are located. If you find after you get everything up and running that your reception is actually worse than when you started, or you are hearing pagers and other junk, a filter is going to be needed. PAR electronics sells them - and while they tend to be a bit pricey, you get what you pay for.
This should start you thinking...best regards...Mike