Asklemmy

It can be daunting to get into the hobby, there are a ton of niches.

To start: where are you? I'm in the USA, so that's where my experience is.

License: required to transmit on the ham bands; you can listen without a license.

Range: are you looking to talk to people in your city/region? If so, a cheap "walkie-talkie" style (called "HT" in the biz

best avoid "walkie-talkie") is a good place to start. These VHF/UHF (very/ultra high frequency) radios are affordable

something from Baofeng(~$30) or similar will work just fine, though they are often looked down on (I have one

for the price, it's great). You will have the most luck if there is an active ham scene in your area, in large part because they may have a repeater, which can greatly extend your range. Many regions will have scheduled "nets" where you just go around and chat.

If you're looking for the ability to chat with folks on the other side of the world, you'll want to look into HF (high frequency). This is much lower frequency, thus longer wavelength, than the handheld VHF/UHF HTs. So...the antennas take up a lot of space. Mine is 52 feet long, in the attic. And the radios are much more expensive (more like $1k new). ICOM 7300, Yaesu FT710 are popular entry level units (but you also need power supply, cables, and antenna).

That said: if you just want to listen to HF, the antenna doesn't matter as much at all, and you can use an SDR (RTL-SDR probably works?) for listening. You can probably also find a used shortwave radio that covers some of the HF ham bands.

My recommendation would be to find a local ham group and see if anyone will let you use their equipment. In my experience, hams are very often excited to do this, they have a new buddy to play radio with. Many radio clubs have club equipment for members to use and often gather and set it up during events, especially ARRL's Field Day. There's nothing like getting hands on with working equipment set up by an experienced user to see what you really like.

Licensed hams can supervise non-licensed users, so you can get on the air before you have a license if you have a buddy with a callsign willing to let you at the controls.

Especially since OP asked about having a "radio buddy," I think this is the way to go about that.

Disclaimer that I'm still a noob, too.

I gave my main recommendation there, for transceiver. I haven't done the research to have a model or brand in mind, but a cheap SSB (single side-band) radio seems like it should exist, given that you can make such a device with just 7 transistors. Any remotely modern computer will be able to generate an audio signal that, when mixed up to RF the way a SSB radio does, will look like the mode of your choice. Software-wise, I've really liked working with GnuRadio so far.

Amps go for a lot more new, because they have to handle both radio frequencies and >100W powers, and do so without causing distortion. Ham radio is a dying art, so poking around for ones at estate sales or similar seems promising. 100W is generally the recommended minimum if you don't want to be frustrated.

For the feedline, assuming you're doing coax, the design tension is between bendability and DB/meter attenuation. For radio 50 ohm impedance is standard, not 75, so you can't reuse stuff from cable TV without transformers. (Impedance matching is very important, as you'll learn getting a licence)

For the various accessories you may need to connect cables, amps, antenna wires and maybe filters, Amazon. They even have the obscure stuff I've needed for my direct sample radio.

All the prefab antennas I've seen seem ludicrously expensive, given that it's a chunk of ordinary metal, so probably skip that and cut your own. Antenna recipes are all over the place on ham homepages. If you're doing a bunch of non-resonant antennas, a tuner will save you time, but they cost as much as an amp. Everything that works at the high-power end is expensive.