I used to play around with 8051 variants and 8pin/16pin PICs back in 2010, whats the equivalent beginner chips now? I have been out of touch since around 2012, except for pi3/4.
ESP32 or Raspberry Pico, if you want something easy to use, reasonably feature full, easy to interface, inexpensive, and medium form factor.
ATTiny, if you are strapped for physical space and don't have anything super complicated to interface with. Also, really inexpensive. I like it for basic electronics projects where even a Pico would be overkill.
On the other extreme, if you need more complex software, then a Raspberry Pi Zero 2 is a great option. Fortunately, the supply situation for Raspberry Pi has been improving a bit, at last. Sometimes, it's nice to be able to use all sorts of high-level software libraries, and then you hit a limit with the ESP32s and Picos of this world.
You can also mix and match. A PiZero talking to a Pico is a great combo. A ESP32 and an ATTiny can also sometimes turn out to be the more pragmatic choice.
Oh, and if you need even more oomph, then I really like the Raspberry CM4. Lots of nice carrier boards to choose from. But that's really not a microcontroller, so might not fit OP's question.
There are plenty of other boards out there. But they frequently have poor support, or are released only for the vendor to immediately abandon them. Maybe fine for one-off projects, but I generally prefer to stick with designs that last for a couple of years. Much easier to support, if I need to revisit my project down the line.
In addition to what others have mentioned if you're using Home Assistant or an MQTT environment than using the ESPHome tools can make life much easier.
You can also install MicroPython, and with it's new and improved "mip" (pip for micropython) you can easily find drivers for most things. Micropython doesn't support "threads" on the esp8266 as such, but can use uasyncio, which achieves the same goal.
You can find a lot of different dev boards with ESP32, like the one you mentioned. There is other with camera, e-paper screen drivers, smaller footprint (Xiao ESP32). The simplest way to program is using Arduino IDE, but I prefer using PlatformIO on VScode. GCC would work.
The interface is with the USB port, which is used for COM port or for programming
The easiest way to program it would be using something like Esphome. I think Node Red is another tool that greatly simplifys things, but I haven't had the time to mess with it yet.