1. Driveway / Reserved
    No better space than the one that belongs to you, whether you own it or lease it. Only downside are the occasional battles you have to fight in order to protect it, a small price to pay for your own slice of concrete nirvana.
  2. Valet
    The next best thing to having a private or reserved space, convenience level is superior to all other spaces. Some potential for anxiety if you're not comfortable with tipping protocol.
  3. Structure - Robo
    Basically mechanized valet, the cool factor is off the charts.
  4. Structure - Above Ground
    Two of the best things about a structure are also the most challenging - the rigidity of one way direction and large number of spaces in a compact footprint provide great value to drivers needing availability and predictability but could also see them driving endlessly in a maze of ramps and corridors. Still, shelter from the elements gives garages a slight edge over surface lots.
  5. Scenic Overlook
    The lack of well defined spaces allows for creativity. Good people watching. You can't beat the view.
    Suggested by @elooto
  6. Surface Lot
    Everyone knows what to expect with a surface lot, the workhorse of American parking infrastructure. Ease of access and proximity to destination are obvious pluses but unpredictability in behavior of other drivers is definitely a drawback.
  7. Street - Angle
    Combines the ease of a surface lot with the thrill of the on street parking space hunt, these are more desirable because they're often located in quaint Main Street districts where spaces are ample and free.
  8. Street - Parallel
    The bane and blessing of most city drivers, nothing matches the thrill of finding an amazing parallel spot and then nailing the back-in with a crowd watching. Obvious downsides are the relative technical ability required and extra time required, both contributors to errand anxiety.
  9. Structure - Below Ground
    Going underground always sounds more fun than the reality - lower ceilings, confusing layouts and fewer spaces than above ground structures due to the cost of digging down. I'll pass on these most of the time in favor of an on street hunt.