Just fyi buildings with 6 or more units cannot apply for a street permit. So even if you were able to find a street that allowed overnight permit, you won't be able to apply for a permit.

Personally, I find downtown is a complete snoozefest, ghost town to reside since it's a lot of banks, hotels, and shops that close up at 5pm and few residents. It's not as bad as it used to be to live in, but you might find yourself isolated as it will be equally inconvenient for friends to visit from other neighborhoods unless they want to search for a meter. But, for what it is worth, I've never actually lived there so maybe someone can vouch for it being worth the premium.