Hi,
...I would recommend 8051 since you ...
The 8051 is a very old and common controller, it is often used and it is true, you will find much information on it.
I recommend to use a modern ucontroller. For me it´s the AVR from ATMEL. Others are also good.
These are modern controllers with much processing power but low current consumtion. This is a big family with a lot of built in periferals. Don´t be afraid of using 3V3 instead of 5V.
It depends on what you need. Is the design for mass production and price matters, then switch to a smaller/cheaper one. Carefully select the periferals you need.
If its possible then try a bigger to start with, it is not more difficult but it gives you more flexibility.
For USB communication: have a look on FTDI
www.ftdichip.com.
Interface to controller can be UART style or memory mapped parallel bus.
The FTDI devices a very easy to use as well as from ucontroller side as from PC side.
PC drivers available. On ucontroler side it is as easy as can be.
Yes, with a starter kit you are on the safe side...
Hope this helps
Klaus