2022
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 data cable. Each piece is useful for certain applications. If you plan to buy better aftermarket parts (shoulder piece, ear piece, USB cable, spare battery), you can skip the kit and just get the radio.
Everything in this Baofeng UV-5R kit is useful and even necessary at times.
The earpiece keeps your radio from being overheard.
The shoulder mic allows 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.
Other radios There are dozens of different radios that can be recommended, and some will likely be better for your needs. Several new budget radios come out every year, and there are all kinds of better versions or counterparts. If you want easier programming, a larger screen, IP67, better Tx and Rx, tri-band, etc., you can look into other models.
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? Probably not. 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.
$1000 of gear plugged into your Baofeng I'm not kidding. People do this. 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 the comms in your AO will be improved by those or other upgrades, then definitely do that, but I suggest waiting until after you've tested 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, a Part 90 license, and probably actually a cellphone-based push-to-talk app in most cases, but that's for another article.