if you just let that in the money option expire. then no you...

if you just let that in the money option expire. then no you will not make any money, the thing is that you dont really need to get caught up on exercise your option. as if your option is in the money you will be able to sell it. then it is up to the person that buys your option to exercise it.

for your needs it may be easier if you were to trade in options to not let them expire. always making sure that you sell them a month or so prior. effectively then time value around this period will be zero. however there will most likely be some discount on the option, this could be put down as a conversion fee, as it takes anywhere between a few days to 2 weeks for the shares to appear after exercising and option. then if you were wanting to by the stock, you could just do so on market as opposed to stuffing around trying to exercise them.