You note:

"A lot of startups outsource the first iteration (or parts of it) of their web based product(s) to an outsource firm and/or an offshore firm so that they can get something up and running that will be a vehicle for the post Angel or Bootstrap phase of their business."

While you are 100% correct that many startups do this, I think it's the fundamentally wrong way to go.

This is when the risk is the largest. This is when the spec is the softest. This is the primary time that if something is going to go screwy, it can damage things fundamentally and for a long time to come. This is the time where you need yor key players to be close and "smackable" if something isn't right.

Later on, once the foundation is in place, things are solid, and the early decisions are made correctly, it's much safer to spread things out. Because it's harder to do major damage. Not impossible, but harder...

And I mean "smackable" in the least violent sense possible. ;)