Every time you call a Wrangler a "car", God kills a kitten.
Jeep Wranglers generally don't rank up at the top as far as safety goes, particularly in side impact tests. The body design just doesn't lend itself to Volvo-like safety, as the doors do not incorporate a significant protective crush-zone.
For insurance costs, you'll have to call up insurance companies for quotes. It can vary quite a bit from person to person depending on driver history, vehicle type, driver risk, where you live, how often the vehicle is driven, and other stuff. Generally, the newer the vehicle, the more expensive it will be to insure.
The older YJ generation is aging, and while they are easier to work on, they may take a bit more work to make them reliable. There are cream puffs out there to be found though, but can be hard to come by. A fixer upper isn't a problem for the experienced mechanic or the mechanically inclined. YJ's do not have air bags, something to consider when it comes to safety.
Plan on getting the modification bug, so be sure to budget for that. A TJ would probably work out well for you. A little older, but not as aged as the YJ's; a bit more refined interior; plenty of aftermarket support/upgrades; air bags. If you blow all your funds on just getting the vehicle, you may find yourself with the "mod itch" and no way to scratch it.