I'm bad at playing rivers

[Gurravasa]

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Thanks for the advice so far. I see how the checkraise is my best line here.

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Dont bet teh turn. He is not taking free cards that often (most likely never) and he will only raise you when you are behind. That is: 1 or 2 bets will go in when you are behind and 1 bet will go in when you are ahead. Since c/c'ing will have 1 bet going in either way you are better of by check/calling

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Does this advice apply when I c/r the flop? I could see him checking behind a lot then so leading make more sense.

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If you c/r flop you lead turn off course...

[Absolution]

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Because I'm a donk?

I thought I could get more bets in by leading because the other option would be checkraising which I think would scare him away.

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That's not going to scare him away on the flop and if he folds on the turn that's not a bad result for you. As for the river, his most likely holdings are things like JT, a flush draw, a small pp or unimproved A high overcards. I think check calling here will win the most/lose the least because you will get bluffs from the flush draws, the small pp and the weaker J, but not get raised by the overcards (which he should have folded on the turn so they become somewhat less likely.)

[mackthefork]

Looks like he has either a pair lower than JJ or an ace, which he was going to call all the way with, I would bet fold this river, because he will always call with his pair, he won't always raise with an ace, and if you go for the check call, he most likely won't bet it more than he should (imo).

Regards Mack

[Tryptamean]

That is some nice donkin OP.