I use PICs for 95% of my day job, and as a result I have practice in everything PIC from PIC10F to PIC64. I keep example devices in stock for pretty much every device family released over the past 15 years, and most have dev boards where available. I also have _every_ debugger they've released in the past 25 years.
FWIW, my Microchip journey goes back to the General Instrument days of the 70s: Microchip was spawned from the GI Microelectronics division in 1987. Yes, I'm that crusty.
As for a programmer/debugger, I'd say PICkit 5 is the one to go for, not least because it:
o Programs high voltage Vpp devices;
o Has an integrated UART-serial bridge;
o Can power devices for tinkering about;
o Will program every MCU in Microchip's line-up
o Will debug every MCO with on-chip debugging (almost every chip over the past 15 years).
Neither the Snap nor the PICkit Basic have a high voltage programming mode, which excludes some old chips, and also imposes limitations on newer chips sharing a GPIO with the reset (MCLR) pin, not big deal unless you're desperately short of pins.
PICkit 3 would be a mistake nowadays. The latest IDE has dropped support for Gen 3 programmers and debuggers, and support for new devices stopped some years ago.
Gen 4 and Gen 5 programmer/debuggers support all chips, barring the Vpp limitation of Snap and PICkit Basic.
o Gen3 includes PICkit 3, ICD 3, RealICE, PICkit-on-board3 (PKoB3 integrated onto older dev boards)
o Gen4 includes Snap, PICKit 4, ICD 4, ICE 4, PICkit-on-board4 (PKoB4 integrated onto newer dev boards)
o Gen5 includes PICkit Basic, ICD 5.
Another approach, if you're only interested in the 8 bitters PIC12 thru PIC18 released in the past 15 years or so is the Curiosity LPC board DM164137 for 8 to 20 pin devices. This has a DIP socket and PKoB4 programmer/debugger with a handful of LEDs and buttons.
For 28 and 40 pin DIP PIC16 & PIC18 devices, there's the Curiosity HPC board DM164136. Again it includes the PKoB4 programmer/debugger, and a few LEDs and buttons.
Both boards include a UART to Serial bridge integrated into the programmer/debugger. You can program your device on the board, then put it into your own circuit. You can also wire up the debug pins into your own circuit, and debug your target in its target environment.
Almost all PIC10 through PIC18, even newly released ones, are available in DIP. Only the higher pin count devices (over 40 pins) aren't.
For PIC24, dsPIC, and PIC32 generally need purpose built dev boards or your own design with an external programmer/debugger. For a while about ten years ago, there was the Microstick I and II that supported numerous 28 pin PIC24, dsPIC33 and PIC32 in DIP packages. There are also several 16 bits & 32 bit PIC32M available on PIMs (plug-in modules) that plug into the Explorer 16/32 board.
Unfortunately, no new PIC24, dsPIC or PIC32 have been released in DIP for some years, although those that are are not EOL.
One of the best things about Microchip is that as a general rule of thumb they don't EOL anything. Very occasionally a device will EOL, but that is due to things like them using an esoteric package that they can't make anymore.
However, one of the worst things about the Microchip ecosystem are the MPLAB X IDE and MCC frameworks, and it's become worse in the last year or so. My suspicion is that's because anyone who knew anything has been shipped off to work on the new VSCode implementation.
Unfortunately the VSCode implementation is even more bleeding edge than MPLAB X.
Something to note about the all 8 bit PIC cores is that their cycle time is 1/4 the clock speed.
The 16 bits PIC cores' cycle time is 1/2 clock speed.
All 32 bitters are 1:1 cycle time and clock speed.
Whether it's an archaic architecture or not isn't necessarily relevant. The first functioning ARMs out of the foundry came out over 40 years ago now, yet the basic underlying architecture pervades to this day, with some tweaks.
The same applies to the 8 bit PICs, with only 9 years ahead of ARM. I'm pretty sure we don't refer to ARM as "archaic". 8 bit PICs have undergone a number of improvements to their core architecture over the years. They're still regularly releasing new devices with new features, including some substantially more complex programmable logic on chip. For PIC16, it's these peripherals that keep it going.
PIC18 had a core facelift a few years ago with vectored interrupts and DMA, that was quite a shot in the arm for the product line up (no pun intended), and again they enjoy many of the same peripherals from the PIC16 heritage.
If you're programming the 8 bitters in C, the archaic nature of the core, particularly bank switching, won't affect you at all. But if it's assembler you're after, I can't really recommend these 8 bitters as a good introduction.
PIC24 and dsPIC30/33F/33E are 16 bit and use a rather pleasing architecture, a million miles away from the 8 bitters and their pesky bank switching. They're definitely not RISC, enjoying tons of addressing modes available to most instructions.
PIC32M is the MIPS core, so although it's the best supported PIC32, it's a dead end as far as development goes: MIPS' owners have switched to RISC-V. PIC32C is the ARM processor, and is the new kid on the block in PIC32 terms.
Regarding low power, it's all about experience, experimentation, and knowing your way around a datasheet. I did a
sub-microwatt LCD clock with a PIC a few years ago, which shows what can be achieved. More recently, that technology found its way into a novelty wrist watch.
There are some interesting new developments coming out of Microchip, such as the dsPIC33A and PIC32A series. These are their own 200MHz 32 bit core, and it's not ARM, MIPS or RISC-V. I've been working with these chips intensively recently, and for raw compute in DSP applications they're difficult to beat in terms of efficiency. As well as a 72 bit fixed point DSP core, they include a double precision FPU. What really floated my boat as a game changer in my area of mixed signal work is that they have sin() and cos() in silicon, 4 cycles each, although with instruction interleaving you can get that down to a single cycle.
So that's my take. TL;DR PICkit5, or one of the 8-bit Curiosity LPC/HPC dev boards that I mentioned.