Hi,
Thats an often asked question in this and other forums, and there are , I'm afraid, as many differing answers.
Software wise, many say start off with assembler as this will teach you much more about the actual pic chips architecture, but as you progess onto the top end projects you will have to move onto C for things like USB, SD cards, Ethernet CAN etc. as Microchip has only produced software for them in C.
However to start with, the lowly pic16F 8 bit chips will serve you well and there are countess example for the on the web.
Microchips Free MPLAB development system includes an Assembler and you can download its free C compliers for whatever pic chip family you get .
For a dev board, I would say look for one that is expandable, rather than having countless leds already on board.
There are many around but be carefull of some ike the Mikroe boards which are not 100% compatible with Mplab, not a problem in the early days but can be on the higher projects.
Have a good search on this forum and also a look at this Sticky for some futher info. Its mostly good but the programmer info is out of day - simple replace it with the Microchip Pickit2.
https://www.electro-tech-online.com...wcomers-please-read-pic-regarded-upd-0xd.html
One further route, if you are into doing your own wiring /soldering etc, is to build you own dev board.. to start with you only need a simple psu, a few leds and switches and an lcd + a pickit2 - a pcb version of mine is here but my original was on stripboard hand wired.