Parking right in front of your desired store does indeed happen, same as winning the 50/50 at the church bazaar happens. But just because it happens doesn't make it a great investment strategy.
A business that relies principally on the 2 customers per hour the one prime parking spot out front might yield is a business that is either extremely high end (in which case the customer can afford a dollar for the privilege) or going out of business soon.
What I think is really underestimated is, ironically, how shitty it is to have the tantalizing possibility of winning the parking lottery dangled in front of your face, but to lose it 99% of the time because of a mismatch between the supply and demand.
This is why parking at Costco sucks - everyone jostles for the prime spot by the door on the hope that "maybe I'll be the lucky one!" and then spends a quarter hour in stop-and-go parking lot traffic with every other sucker. Meanwhile, if you park at the edge, you can park and walk in in five minutes and experience zero frustration.
Similarly for the Market, what sucks more than anything is that when you get into your car to visit Bottega, you don't know if you'll find parking in 10 seconds or in 10 minutes. You don't know if you'll be the lucky winner of the free spot or if you'll have to pay at the garage. 99% of people will have a bad experience in order for 1% to have a good one.
Imagine if you had a restaurant where 99% of the time, you get a terrible-tasting dish that takes forever to come out and may either be free or $30. How often would you feel like eating there for the 1% chance?
It's much better if 100% of people have a reliable, predictable experience.
My suggestion: I'd get rid of the lottery and use pricing to make sure that parking is a dependable experience. I'd price the on-street spots much higher than the garage spots, so that for those who really want it, there's always a spot available on the block. I'd price the garages lower than street parking, but high enough that space is reliably available for anyone who's looking.
Now, instead of visiting the Market being a gamble, you know before you leave the house how it's going to be; if you really want the prime spot, it'll be available for you; if you want cheaper parking, it'll be available for you. No more guessing, no more gambling. There may not be any amazing parking experiences, but there are also no terrible ones: You know what you're getting every time.
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I've always struggled with reality. And I'm pleased to say that I won.
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