[ymu]

With the very weak bets you've been making so far a push might be OK. He only has to call about 25% of the time that he would call a standard value bet to make it +EV.

I'd prefer to bet it properly on the flop and turn though. As soon as you flop the 8 you need to be thinking about how to get his whole stack in by the river if he's flopped enough to call any bets - especially if he's drawing, you need to make him pay more as you won't get any more on the river if he misses.

300 on the flop puts 900 in the pot. Another 650 on the turn puts 2200 in the pot and then you can put him all in on the river easily.