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Then again, 8.p18 9.s15 10.r19 11.n17. But that could be the beginning of a combo attack, perhaps: 12.l11 13.l12 14.o12 15.k10 16.l15 17.o13 18.m17 looks good for Black.
I think Black was winning by move 7, and lost it on the 8.q19 9.n17 exchange. He had plenty of space across the bottom, and White had a linear commitment. Exploring some of the variations above support the idea that Black was winning. 8.q19 was just too unbalanced. It let the White line get to the bottom. I looked for a good move for Black on move 10, but didn't find one.
Given the indicated combo attack, starting now with 10.l11, I had planned at the time to respond 11.n8. Then 12.o12 13.l12 14.n14 would give black control of the center, and I would have had no choice but 15.h14. I think I can probably win from there.
By Medcalf defense after 8.p18 9.t18 10.t20, I understand you to mean 11.r19 12.r21 13.p20 14.o20 15.n21. Is that correct?
I also guess that the continuation that you both have in mind is 16.r14, threatening both q12 and s16.
I don't think I would have even thought of r14, because it's a buddied peg with Q14, and kinda far from the edge. The first two replies to check are 8.p18 9.t18 10.t20 11.r19 12.o20 13.q21 14.r14 15.s13 and 15.s15. Do they check out? 15.s13 16.s16—mmm, Black has just enough room to squeeze thru, I think, so I suspect the other one (15.s15) would be better for White... but it's not clear to me. Anyway, the q12 threat doesn't really look like much of a threat: 16.q12 17.p12 18.l11 19.l12 20.n7 21.k10... looks like a White win, thanks to the c3 peg.