RE: dumb question
Lots of material on field dressing, aging, butchering, etc, search it out and by all means ask the questions you have not found answers too, we have all been their so don't be affraid to learn from our mistakes.
Like said aging is really up to each hunter. If you can hang the deer in a controlled enviroment of 34-40 degrees than it will not harm it any way. If it freezes it does nothing to age and if it gets to warm you run the risk of spoiling. I would say if your in a position where the meat can not be controlled, take it to a meat locker and have a butcher cut n wrap it for the first time. If you want to tackle butchering yourself try to enlist the help of an experienced hunter and DIY butcher. It certainly isn't hard but it maybe a bit more than you can handle in your first hunting season. I would suggest pay more attention to learning how to hunt safely and effectively in your area, than worry about cutting up your harvest(s).
Cost vary but as mentioned pick a reputable butcher and if you have to pay bit more than so be it. The last thing you want is not your deer back or it done poorly after all the time and effort required to get the animal. Ask here what hunters prefer of cuts when taking there deer to a butcher and match that with yours or your families likes and dislikes. If your not steak eater's or sausage eater's nothing worse than having a pile of that meat to have to struggle through before next season.
One of the most important things to good quality outcomes on the table is a clean harvest and proper field care, so practice your shooting and learn all you can about field dressing and care of the animal after the harvest.
Best of luck!