Blackjack Card Counter here - should i be concerned with comps and 1099s?

I am an amateur card counter and 90 percent of the time, I bet table minimum ($5.00 or $10.00 per hand). However, there are times I raise my bet to $100.00 per hand and the pit boss usually does not give me credit for these larger bets. If I speak up for myself, would I attract un-needed attention and risk getting backed off?

You are getting a 10-1 or a 20-1 spread and you're concerned about a lousy $10 comp?? Your aim is to make money and with a spread like that you will (assuming you can count in the real world and you know the changes to basic strategy based on the true count). Don the Dentist

You might start off betting $25. Bet that the first few hands after buying in and the pit might mark you as a $25 player. Then drop down and up at will. Try to bet more when he's around but betting according to the count trumps pit boss observation.

I wouldn't bother with the comps, but if you make a jump in your bet from $5 to $100 even if the pit boss doesn't notice the eye in the sky probably will. I would guess after a few times doing this while sitting at the same table, the bit boss will get a call from upstairs telling him to push you back the next time you do it. Have you tested this strategy for long periods sitting at the same table or do you jump around? Maybe it is still too low stakes for the casino to bother with.