The short version is that legally, yes you do, but in a practical sense, no.
City of Orlando set out rules about two years ago for what you need in order to operate in Orlando, including a $30 VFH permit, commercial insurance etc.
Uber on the other hand doesn’t believe they are necessary, so they will not tell you this, or will say “you do not need anything extra to pick up in Orlando” (unless you want to pick up at MCO).
That means that if you get caught by VFH picking up without a permit (you won’t get in trouble dropping off), you will get a couple of tickets and fines in the $500 range, and in rare cases you can have your vehicle impounded.
However, Uber will pay these fines for you. You just send them the details and their legal team will take care of anything.
How can you avoid getting ticketed? Really, you can’t.
People get ticketed when they stand out – eg picking up outside The Beacham while blocking traffic will get you in shit pretty fast – that’s why picking up downtown you’re better off parking on a cross street and having your passenger walk to you.
More common these days is to get ticketed in a sting. This is where VFH will pose as an Uber passenger, request an Uber, and then ticket them when they show up.
As well as City Of Orlando, Osceola have started ticketing very aggressively at Gaylord Palms.
So is it something to worry about? That’s for you to decide. There are tens of thousands of Uber drivers in Orlando operating outside the law as it were, so really you’re just one of many doing the same thing. The only issue is that at one time the city was notifying people’s insurance companies that they were making pickups, and this can get you dropped and your rates will likely go up. But that’s rare.
Why don’t drivers have the permit? Because once you include licences, insurance etc the outlay isn’t $30, it’s about $2000. Is it worth that to make 65c a mile? When Uber will pay the ticket anyway? Almost certainly not.
As ever, proceed with caution!