Depends on whom he’s fighting. A serious Deadpool could take out most street levelers with a fair, but not excessive bit of difficulty. A few examples just to get an idea.
Spider-Man (Peter Parker) I honestly think Deadpool could take out the web-head. Deadpool's shown himself to have way above average accuracy with his handguns. Tagging Spidey just once would give him enough to fire off one or two more shots and take him out of the game.
Captain America (Steve Rogers) There have been a few instances where they've fought, but never when Deadpool is serious. I forgot where, but I recall Cap saying that if Deadpool stopped mucking around, he could be a serious threat. Based on feats, I agree with that and would say he's got enough skill to take out Cap.
Daredevil (Matt Murdock)Now, I doubt Wade will land much on Daredevil, but there isn't that much Daredevil could do unless it was close-range. If Daredevil got in close, I'm sure Wade could find a way to make enough noise to distract Matt (even if it's just for a split second. That's all a focused Deadpool needs). Not to mention, Deadpool probably smells terrible. I imagine that there isn't much time for showers in his line of work. Essentially, I'm saying Deadpool could overwhelm Daredevil's senses.
Wolverine Here's the one I think Deadpool would have the most trouble with. Wolvie's healing is almost on par with his own, and his weight (from the Adamantium) would probably help him tank all of Wade's bullets. This particular fight would go to Logan.
If you want examples for other street level guys, I'll try without exaggerating his bloodlusted skills.
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