I was there last year while in Tampa for a few days.
There are several local shops that do their own rolling, which is neat... but I don't think it will blow your mind. Ybor city isn't so big that you won't end up wandering the whole whole thing and seeing most of them.
I was warned that Ybor city is a bit shady at night, and it was. Not really the place to be wandering at 11:00 pm if you have kids. There are quite a few, uh, gentlemen's clubs on the main drag. Turns into a mixture of thugs, drunk frat boys, and, well... um, strippers wandering around trying to get you to come into their clubs. (The strippers, not the drunk frat boys.)
Now I'm making it sound awful, which it isn't. But unless you like that sort of scene, avoid it at night.
One of the cigar bars (can't remember the name and can't find it online) was right on 7th ave, which if I remember correctly is the "main drag". My pal and I smoked Ashton VSGs and drank beers on the sidewalk, while our fiances sat there and got impatient. Good place to people watch.
Anyway, I don't really think any of the cigar places will blow you away. One thing you SHOULD do, however, is hit Tampa Sweethearts, the shop owned by Fuente. Not because it is impressive. It isn't, at all. Not remotely. In fact, it is a largish old building, and the only part open to the public is a small lobby. In fact, it's a dump. But it is a dump where you can buy things like Opuses, Sharks, and other hard to find cigars... at MSRP. Woot. Nice to grab a Shark for $9.80, an Opus for $11.25, a maduro Hemingway Sig for $6, etc., etc. There were limits (like two of each for Opus/Anejo and four for maddy Hemingways) but it is still worth stopping by.
And get a pitcher of Mojitos while at Columbia. They use fresh sugarcane, squeeze a bunch of limes... dang good.
In the Columbia Restaurant there are 2 rollers....I forget the brand they roll, but their cigars are pretty good.
Up the street, on the same side, is a place called La Herencia. They roll their own brand right there in front of you. Last time I was in there, I think they had 3 or 4 rollers working. Cigars are......ok I guess.
It's kinda cool but not that big of a deal.
NOW, here's where to go, even though I have never been in the location myself. Their cigars are very, very good. I only have 2 left and I am marinating them......