Go Simple or Go Complicated?

So here I am busily learning how to make a WordPress Website work. There is a lot of detail here. Is this a good thing or a bad thing?

I can see someone just wanting to get a blog up fast and never mind the fiddly details. I was like that when I started my blog.

But if you want a Website that has lots of features, you have to put time in to figure out how to do it all. This is what I am working on now for Ride North America.

Just today, I read a post in a list I subscribe to in which the poster wants an easy way to set up a photo display site for someone else.

Just how well does it work out to start by doing things the easy way and possibly having to do it all over again later versus biting the bullet and going sophisticated from the start but possibly never needing the high-end features?

For a given case, the answer might not be obvious.