Ok some areas for you to look at first:

1. Digital Modes: Have you explored digital modes like PSK31, JT65, or FT8? These modes involve encoding data into audio signals for transmission, which you can decode using software on your computer. It’s a great way to marry your programming skills with radio communication.

2. Software-Defined Radio (SDR): SDR technology opens up a world of possibilities. Consider tinkering with SDR hardware like RTL-SDR dongles and developing software to analyze and process radio signals. There’s so much you can do in terms of signal processing and visualization.

3. DIY and Homebrewing: Building your own radios, antennas, and accessories is a fantastic way to learn and experiment. Whether you’re designing custom circuits or optimizing antenna performance, there’s no shortage of projects.

4. Satellite Communication: Ever thought about reaching out to satellites? Satellite communication involves tracking satellites, designing antennas, and mastering operating techniques.

To get started

ARRL Technicians License HandBook

ARRL General License Handbooks

“Ham radio crash course” on YouTube

1. Radio recommendations are hard, if your interests fall into the above at your cost points I would look at xeigu G90 or other Xeigu models.

2. Plus Digirig cables.

3. Make your own antenna with a wire soldered to coax connectors.

4. Coax

I think that would be about $500, a little over

For $200ish I would do

1. the ARRL handbooks

2. QDX Transceiver http://qrp-labs.com/qdx Or other from qrp labs.

3. Make your own antennas

4. Coax

Final bits:

RTL Dongles and that genre are good for listening across the bands before you have your license to transmit and pretty cheap. Check out SDR++

Get plugged into a nearby club membership may get you loner equipment and regular participation will speed up learning.