I was in the same boat last year. 38 year old city boy who discovered the joy of hunting. Pigs, axis, sika, etc. Frankly, if possible, just lend a hand or two to those who are dressing something already. Two or three times, and you're probably ready to skin and cut off the lower leg portions. Next time or two, it'll be time to gut. I'd recommend a small pig - 40 lbs or so as a first. They smell on the outside, but in my experience, they small better on the inside than a large axis. It's also a very manageable size. Don't have to worry about guts going everywhere and they're easy to manhandle.
Good luck, keep at it (we're Men afterall), and enjoy it for what it is.
ETA Also, what for cuts and just be sensible with regard to sanitation. You can catch a bug but you're not going to die or anything, usually. You'd be amazed the number of cases of Giardia are misdiagnosed as food poisoning.