For your ??? on the gun/bow. Most people find the gun much less complex to learn and fill tags. As you said the shotgun is a more versitile weapon. Well some people can drop game birds deer etc with a bow. But the chances of a less exsperianced hunter hitting a rabbit or game bird between the 2 weapons just count the odds in the ammo. Bow=1 projectile. Shotgun 100+ easy with lighter loads at decent yrds.
Just remember make sure you check the regulations about gun plugs or amount of ammo you can carry, even type, before you grab some shells and go into the woods. Most states require your gun to be only able to hold 3 shells, in chamber and the magizine, (many guns that are able to hold more normally come with a plug, mossberg's do I know.)
Archery seasons do normally run much longer, and are considerred much harder to fill tags. But I think most (well at least I do) put much more time in preparing, and the actually hunting for bow than gun.
I most of the time hunt solo myself. The kids don't have patience, the wife hates the cold. Just a tip might help if an accident does happen. Be prepared read up on some 1st aid prior to goin into the woods. Could be very useful.

As for the books you "should read" I think that the internet could be so much more profittable. Books have the habit of being wrote by 1-2 authors, so their hunting techniques are kinda bias. You know 1 person telling another the only way to do this or that. Or at best a couple veiws on a situation. With forums like these and some articles that are samples sometimes at magizine sites can offer alot.

And for being a "city boy", its not the place you grew up, or where you live. To me its the attitude or hunting "air" of a person. A responsable hunter sees a deer, feel confident and takes a shot if he feels he can make the kill. A "city boy" sees a deer that most hunters have a good idea that at that range with that gun/bow/ ammo /situation and wait, or attempt to change the odds to their favor. The city boy unloads his gun in the general direction of the animal, even as its bolted WAY out of range reloads ASAP and keeps firing. I have seen many country born and living "city boys."
Guess I think the difference is do you go "to kill something" or "To hunt something". If its the latter welcome to the woods. If its the prior. Find an ant hill and a magnifying glass. No offence meant.

PS for lease/private land check some classifieds. Or if you have the extra $$$ put 1 in the local papers or an area you would like to hunt. Many people lease/rent land after the summer season or the farming "off" seasons.