Re: A rag or 98o?
Basing your judgement on the jam-or-fold tables in Chen and Ankenman's "Mathematics of Poker" is perhaps not a bad thing to do. (These tables contain the optimal play of the heads-up jam-or-fold game.)
According to Chen and Ankenman's tables, for A2o it is better to push stacks up to 29.2 BB, whilst for 98o one should prefer jamming over folding for stacks only up to 20.5 BB. Higher A-rag hands (A3o, A4o etc.) all have even higher jamming power.
According to the same tables, a hand like T9o has equivalent jamming-strength as A3o (EV-positive up to stacks of 31.9 BB).
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