What sucks about apartment hunting?

I want to brainstorm everything that sucks about searching for an apartment. Why is it always so painful? Does it have to suck so much? I have some ideas but I haven't done this in almost a year so the pain, it is not so fresh.

Here's what I've got so far:

• Keeping track of everything. Losing phone numbers, did I call that one back, wait is that a duplicate or another unit in the same building?
• The uncertainty. Will this landlord suck? How can I find out? Is the neighborhood ok?
• Finding some place close. What's the commute time? Where is the nearest grocery store?
• Coordinating with roommates or significant others. Will they like it? I guess I could email them...

In the past I've had a few solutions to this, as I'm sure everyone else has too. The first time I searched for a place I didn't really keep track of anything except in my email inbox. It was kind of a disaster. By the time I picked one place I had already lost the others, but didn't find out until after I called them back. The next time was a little better but still I think my roommate and I mostly communicated via email. The third time I built a tiny Rails site for my girlfriend and I to keep track of stuff, but I never really fleshed it out and we kind of just sat next to eachother on the couch and shared craigslist links over IM.

What I'm looking for here is everything else that sucks about searching for a place and why, and what kind of solutions you've duct taped together to make it work. Websites that make any aspect of it easier would also be super helpful. Everybody who responds gets $2.00 of Remindlyo credit :)