Biggest thing ollied was a four block where each block was the size of a two stair, so about eight stairs? Biggest actual stair set and not blocks I’ve ever ollied though was a seven stair.
Even back then I was never really a stairs or gaps person, when I would try that kinda stuff I’d always just get so psyched out and it would just always feel like a constant mental battle to even try it and commit on top of that. I pretty much would have to force myself to skate stuff like that when I did, instead of actually wanting to skate it, if that makes sense. A lot of the dudes I skated with back then in my younger days were really into stairs and gaps so I found myself skating that kinda stuff pretty often even though deep down I really didn’t want to. I must admit it would feel REALLY good to ride away though after the mental battle to even try it and the physical battle to get it, but it was still never for me. I grew up skating when stairs and gaps and handrails were more of an essential thing you had to skate if you wanted to get “good”, glad now that’s less the case. Now you got dudes making whole careers out of only skating curbs, it’s great. This would have never been possible in the mid 00s.