Part A - I am on the side of completing as much UX up front as possible. Bad visual design is something that no one can ignore. I think that ideally before you

Part A - I am on the side of completing as much UX up front as possible. Bad visual design is something that no one can ignore. I think that ideally before you even have done the "black-text-on-white-background" prototype you start with UX. Part B - Steve Krug has a couple of simple concrete usability books. Other than links I have seen mentioned. http://ilovetypography.com/ http://ilovetypography.com/ learning good type will help a ton with design http://www.useit.com/ http://www.useit.com/ Jakob Nielsen is kind of the godfather of usability, some people love him, some hate him, either way you will learn something from this guy. Also, going through tons of websites and critiquing them by yourself or with peers, writing down everything that works well and doesn't work well, that you would change. Do little usability tests on your sites, even on sites that aren't yours with family or peers. Part C - I don't know as much about startups. I do know that having a designer on hand is much nicer to work with than outsourced. Ultimately I think it would be like dealing with anyone else outsourced in terms of reliability. Part D - I actually started as a designer, and IE 6 crushed my soul. I am still very interested in UX though. I think starting as a programmer, I would just try to recreate designs you think are appealing. I would also try to learn the grid system. Use CSS frameworks as training wheels that have a solid grid, and decent typography (eg. Blueprint). I started constraining myself to HTML and CSS, and I think you should too, leave Photoshop alone until you can make decent designs in just HTML and CSS. Then, when you are completely comfortable using the two, then look to PS to add details that you can't achieve otherwise. The big obstacle you will run into, is that you will feel like you aren't making as good of designs as designer X. Design in my opinion is much more personal and emotional than programming so don't let that get to you. Good Luck!