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For me, I suggest to get start with PIC, it has suffecient resources online and many practical project to practice as well..
Start by buying a PIC chip (Say 16F624) and lookfor its programmer online (easy to get) build a programmer as well as simple test circuit with few LEDs and push-buttons at in/out ports pins, you may add some touches like LCD or keypad or whatever..
Then, get some tutorial, and follow up to end (along with practice!).
Of course you have to get the Datasheet as well as some application notes related to the project you aim.. (but the most important is the Datasheet!)
Select the language you use to program with (I suggest to start with Assembly!!)
Make projects, ask for help ..
ATMEL AVR family controllers are very good easy and more suitable for embedded applications.
u can use attiny2313, atmega32 or any other of avr family.
the programmer is so easy just search google for "pony programmer"
I suggest to learn Atmel AT89C51, it is compatable with 8051
the internet has many example about it
also, it is easy to migrate from Atmel AT89C51 to Atmel AVR for more complex projects.
Software is free (https://www.rev-ed.co.uk/picaxe/software.htm), you don't need any special programmers (PICAXSE is directly connected to PC's serial port) etc. etc.
I really can't see enything else simpler than that ..
Even if a lot of memnbers may say: 8051, AVR or PIC is very simple, but as far as simplicity is concerned NOTHING can beat PICAXE ..