I'm Tal Leming and I design typefaces and lettering at my type foundry, Type Supply. I also write a lot of code to support the type design process.
I can't pick favorites. I mean, I could but I would change my mind a few minutes later and again and again. There is a huge amount of great typeface design going on right now. Take a look at the Typefacts list of the best fonts of 2013 to see just how many good, new typefaces there are.
I use RoboFont for drawing and production. It is very comfortable to draw in and the extensibility is outstanding. The ecosystem around it is growing rapidly and for the first time in many years I find myself using code written by others to help me with my day to day design work. RoboFont makes my work day so much brighter every day. I love it. I use the legendary Superpolator for interpolation. I use my own MetricsMachine for kerning and Prepolator for getting fonts ready for Superpolator. I use FontLab (the Windows version) for TrueType hinting. I use TTX for studying and repairing font files if a bug ever pops up. I use TextMate for writing code. I reluctantly use InDesign for proofing desktop fonts. It's a nice program, but it's way more powerful and complex than what I need to make simple proofs. I use Safari, Chrome, Firefox and IE for proofing webfonts. Finally, I use lots and lots and lots of Python to help me with just about everything.
Ideal work environment
There doesn't seem to be a single "Aha!" moment of inspiration in type design. In my experience it is a cumulative process. A chord change in a song can inspire a feeling that I want in a typeface. A session of sculpting Play-Doh with my children can inspire a letter shape. A walk on a warm day can inspire a rhythm that I want to see in a text block. These bounce around in my head for days/months/years and eventually they start to glob together and take the form of a typeface.