Which radio should I get?
Sure, there are reasons to get awesome $750 ear pro and $100 push-to-talk buttons and huge antennas and $75 cables and snap them all to your encrypted digital radio. If you have reason to believe your comms in your AO will be improved by those or other upgrades, then definitely do that, but I suggest waiting until after you've tried and failed with the least prohibitive setup and kit, if you have that luxury. At least get appropriate and robust training or experience to make sure you're maximizing your tools' capabilities.
If the $45 radio kit doesn't work and your situation requires better communication tools, it warrants getting training first, then a better antenna or radio ... and probably a repeater, and probably actually a cellphone-based push-to-talk app in most cases, but that's for another article.
What kind of radio should I get? Two Baofeng UV-5R 8w kits. Nobody regrets owning one or two of them, and you can always get something you like better in the future because you saved a lot of money. Get the kit with the extra battery, the shoulder mic, the over-the-ear headset, and the USB cable. Each piece is useful for certain applications. If you plan to buy upgraded aftermarket parts (shoulder piece, ear piece, USB cable, spare battery), you can skip the kit and just get the radio.
Others will recommend the BF-F8HP or some other version of Baofeng or TIDRADIO or Pofung. These are also ok, but if you get the Baofeng UV-5R, you might have a better time if you'd like your friends to help you program it.
There are a few interesting things happening out there, and some may find certain digital radios to be their best option. Talk to your friends about what their goals are, what you might run into on the airwaves, and what your time and financial commitments are.
Do I need to buy an upgraded antenna? Maybe. It's a good idea to test the stock antennas for your needs before getting a "better" antenna which may come with its own downsides. If you can't communicate with your stock "rubber ducky" or whip antenna, you can find all kinds of resources that recommend better antennas. Before doing that, I urge you to try a few things.
Keep the antenna vertical while transmitting (Tx) and receiving (Rx)
Hold the radio in your hand because your body grounds the antenna.
Hold the radio high above your head, go to higher ground, or stand on something.
Consider grounding the antenna with a counterpoise or, seriously, a licked finger on the correct screw.
Be sure to use effective speech and communication techniques that you can learn in appropriate trainings.
Get out of your car.
Get a 3-meter SMA cable extension, and string it into a tree (height is might). This is obviously more cumbersome and less convenient, but it will work where the best antennas won't.
Do I need an aftermarket push-to-talk? Let's rule out Bluetooth push-to-talk buttons right off the bat. They will disconnect from the device. Like everything else, test your stock kit until you find out where it fails. If it's inconvenient to key your PTT button on your radio or mic accessory, get an aftermarket PTT. The cheap ones have downsides, but they do work, and the quality ones can be incredibly expensive.
Check out these other recommendations for other kit and safety tips.
Everything in this Baofeng UV-5R kit is useful and even necessary at times.
The earpiece keep your radio from being overheard.
The shoulder mic allow you to keep your radio on your belt or in a bag.
The data cable allows you to program the radio in ways manual programming doesn't allow.