My two ICD-3 programmers no longer work. Had to buy an ICD-4.
I still occasionally use my old ICD-2 (aka 'the puck'), although I've replaced the driver IC a couple of times as it's a know weak failure point, and a couple of PicKit3's. I've also got a couple of Pickit4's stashed in a cupboard just in case my PicKit3's die (the 4's are way faster!). Never had issues with PC drivers, especially for the older legacy PIC16's, PIC18's and PIC24's based PIC's! Only the newer dsPIC's and PIC32's need the newer dev tools, but even the PicKit4's support all those ... and at a fraction (currently less than $90 direct from Microchip) of the cost of the ICD-4 or $2K ICE.
Apart from the interfaces and optimised compilers, everything else from Microchip is free (MPLAB-X, etc). You should try getting into the PIC CCS C Complier nightmare (NOT!) ... updates every week to fix bugs and add new micro support and introduce more bugs, then every annual major release is another $300 ... just to get bugs fixed they introduced in earlier versions, and the code is locked into their own libraries, etc!
Just had to buy a Segger J-Link Plus to do a customer supplied project (Renesas based!) update and firmware feature add to their product. That was the best part of $1200 ... I just added it to the invoice!
I feel your pain, it can be a nightmare, but after 35+ years doing this, I know how to make use of older tools on older OS's without spending much on 'newer' tools that offer very little productivity ... unless the customer is willing to pay for it! Got a lot of dev tools over the years off of the back of quoting for a project
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