[admiralfluff]

situation 1:
1) I'm envisioning a 35/17/1.5 type player here. Easy fold. Easy fold against almost everybody.

2) This question is either poorly worded and makes no sense, or I am illiterate.

3) I start thinking about a 3bet around 66, and usually will pop 77.

situation 2:
I fold preflop almost always. I pop 55. 44 is borderline, but usually fold. I don't know what I would do on the turn without reads when he calls the flop. If I don't have specific reads, other than that he is a crazy lag, I'm getting to SD so I guess either b/c or c/c. I actually don't think it matters much.

I think your edge in these borderline situation comes almost entirely from dead money preflop. Having position and skill will only adjust where the border is.