I also think that the stuff that came out of Rails Rumble looked pretty awesome especially done in 48hrs. I created ShelfLuv in about that timeframe as well and see both sides of the coin to use your terminology.
Part A: To me the design and UX is first and foremost. Especially w/ a hackathon - think of your product like a runway fashion show. On the front side it just needs to look and work perfect. Under the hood for me, out of the gate doesn't matter as much as long as it works and isn't slow to the point that it affects the user's perception of the product. I typically try to think of the user's interaction/perception/experience first. Mockups in Photoshop are pretty useful to me, but so are HTML mockups. It all depends on what I am trying to achieve. A visual experience - playing around w/ that would be best served to me by toying around in Photoshop. An interaction experience, mocking variations of that in jquery is best because I can click around. I can touch and feel my app. However I mostly start everything with sketches on pieces of paper or my notebook. I try to draw different variations. I look at how other webapps/apps do them. With ShelfLuv there werent many ideas or variations. I didn't start having variations until I had something working to show. If there's nothing to show yet, I feel that people have no baseline with which to compare. It's a lot easier for most people to say A is better than B, than to just show them B and ask them if this is any good.
Part B - I find that a layperson is immensely useful in this arena. One of my sounding boards is my wife. She's very intelligent but is not what you would call a techie or designer type. Alot of times I just want to use icons but many nontechie people will have no clue what these icons mean. Of course it's a compose icon - it's a pen and paper.
Part C - I would say you can outsource visual design, but it would be hard to outsource the interaction design and how the app works. Interaction is a process that can be very iterative. You try something, it doesn't work and you try it again.
Part D - I am an engineer by training but started focusing on user experience and interaction about midway in my career. I felt like I could have the most impact on users through a great product experience. I started by reading a lot of blogs and sites of great designers. I look at and try a lot of web apps and sites. I also buy a lot of iphone/ipad apps to see how they work and what they've done. Major obstacles for me is that I'm not a graphic artist and I can't design from scratch. I know designers who like to create textures and stuff from scratch and to me I feel more like a cobbler of design elements rather than an original creator of design. I will put this design element together with that element. I'm basically pretty handy at tweaking and modifying in Photoshop but ask me to create stuff in Photoshop and Illustrator from scratch using the pen/brushes/paths and I'm lost.
I also think that the stuff that came out of Rails Rumble looked pretty awesome especially done in 48hrs. I created ShelfLuv in about that timeframe as well and see both sides of the coin to use your terminology.
Part A: To me the design and UX is first and foremost. Especially w/ a hackathon - think of your product like a runway fashion show. On the front side it just needs to look and work perfect. Under the hood for me, out of the gate doesn't matter as much as long as it works and isn't slow to the point that it affects the user's perception of the product. I typically try to think of the user's interaction/perception/experience first. Mockups in Photoshop are pretty useful to me, but so are HTML mockups. It all depends on what I am trying to achieve. A visual experience - playing around w/ that would be best served to me by toying around in Photoshop. An interaction experience, mocking variations of that in jquery is best because I can click around. I can touch and feel my app. However I mostly start everything with sketches on pieces of paper or my notebook. I try to draw different variations. I look at how other webapps/apps do them. With ShelfLuv there werent many ideas or variations. I didn't start having variations until I had something working to show. If there's nothing to show yet, I feel that people have no baseline with which to compare. It's a lot easier for most people to say A is better than B, than to just show them B and ask them if this is any good.
Part B - I find that a layperson is immensely useful in this arena. One of my sounding boards is my wife. She's very intelligent but is not what you would call a techie or designer type. Alot of times I just want to use icons but many nontechie people will have no clue what these icons mean. Of course it's a compose icon - it's a pen and paper.
Part C - I would say you can outsource visual design, but it would be hard to outsource the interaction design and how the app works. Interaction is a process that can be very iterative. You try something, it doesn't work and you try it again.
Part D - I am an engineer by training but started focusing on user experience and interaction about midway in my career. I felt like I could have the most impact on users through a great product experience. I started by reading a lot of blogs and sites of great designers. I look at and try a lot of web apps and sites. I also buy a lot of iphone/ipad apps to see how they work and what they've done. Major obstacles for me is that I'm not a graphic artist and I can't design from scratch. I know designers who like to create textures and stuff from scratch and to me I feel more like a cobbler of design elements rather than an original creator of design. I will put this design element together with that element. I'm basically pretty handy at tweaking and modifying in Photoshop but ask me to create stuff in Photoshop and Illustrator from scratch using the pen/brushes/paths and I'm lost.