If your airplane has a shutter or the ability to close off airflow to the oil cooler, you might want to adjust that as needed to maintain oil temps as close to the magic 180 degree mark as possible. Where I live in Michigan, I just put some Gorilla tape over the oil cooler and it works just fine. Trim the area covered by the tape to regulate oil temperature as needed. Temporary solution for the temporary cold of the the winter flying.
Other than that, I wouldn't worry at all about a weekend trip to MO from GA. CHT's will be a bit cooler than you're used to seeing but there's nothing wrong with them. If you're worried about a cold start in the morning leaving Missouri, try to find a heated hangar at the FBO for the overnight (worth the price) -OR- bring your own extension cord and plug in if you have a pre-heater installed. My personal mins before taking off or running up in the cold bits of winter (or anytime really) is 100*F on the oil and 200*F on the CHT's. Doesn't really take long to get that warm, especially if you've pre-heated. For a cold, un-preheated engine, experts will tell you that's the most damage you can do for an engine. I'm not an engine expert so I believe it. I pre-heat as much as possible. BUT IF YOU CAN'T, just let it idle at 1000 rpm (splash lubrication) or less until the 100*/200* temps are met. Could be upwards of 10-15 minutes depending on OAT. That's a get out of Dodge, worst case scenario. Again, paying an FBO for a heated hangar overnight is worth the price.
Personally, I wouldn't even consider that trip to be "cold weather" yet this year. Just cover the oil cooler and try to pre-heat wherever you stop. Cowl plugs to keep the heat in during a fuel stop or lunch break. The weather moving across the country and clouds this time of year I would anticipate as a bigger challenge. At least in the Midwest areas.
Sincerely,
An O-320 operator in Michigan. (Not as cold as it could be, but cold enough for me)