Villain is huge online winner and mainly plays HU cash but also plays live tournaments as well. He has started fairly cautiously, stats wise he is running 37/26/9.

Think a flat here in position is standard with these stack sizes.

Here is the main crux of the hand I am unsure whether i should be raising a draw like this given we have no showdown value. Having reviewed this against a reasonable get in range we are committed against a shove once we raise flop given the odds we are getting. However this is a texture that favours his range and we dont have many value hands aside from top pair so I think villain would correctly assume we are weighted towards semi bluffs if we raise and react accordingly.

Once i do decide to flat I was then unsure how to proceed on turns. When he checks I feel we could bet small with our whole range though with our specific hand this seems bad if he is check raising a reasonable amount of the time. What cards would you consider betting in our spot and would you ever shove over a turn bet. Basically in a convoluted manner I am asking what factors do you consider in constructing our ranges in this spot?