At the home I work at a lot of the residents have that problem. They take so many drugs that the side effects gang up on them and force them to take other drugs for the side effects. I try to recommend to the doctors as many natural medicines as I can that cause fewer bad effects to occur. I have to give stuff like remeron and megace to people who get nauseous from other things so I understand your pain with your insomnia as, with my ADD, I suffer from it too. More indica heavily dominant hybrids are apparently the best and sativa will just keep you awake. About tolerance, cannabinoids don't cause dependence very easily and the reason for needing more is the CBD receptors that let you get high from
marijuana undergo down regulation (I.e. they just become less sensitive to it, like insulin for a Type II diabetic.) If you are getting to the point where you notice you need more herb for the intended affect, take 1-4 days off and you will notice a marked increase in the effect. The undoing of down-regulation happens in a matter of days. Any residual cravings and side effects from long term use are much milder than most drugs and disappear in usually 30 or less.
Did you know that a lot of the OTC sleep aids are just Benadryl with different names and colorings? Benadryl does make you drowsy initially, but its sedative side effects go away quickly after about 1-2 weeks of consistent use. Most of them are that way, not just diphenhydramine. The prescription and OTC sleep aids cause me to feel drugged the rest of the day. I feel well rested and ready for a new day after I get some good sleeping weed and then every couple of weeks I stay off for a day or two and it keeps me taken care of with less than thimble sized amount of herb (Just enough to slow my mind down a bit). I tend to use a day when I don't have too much to do as my smokeless day so that if I can't sleep until 6am, it won't matter too much.
Sadly, it isn't legal, but it can be grown discreetly and a little can go a long way if you can do with just a push to the Land of Nod. If you need to smoke a 10-ton mallet everyday though, growing your own supply gets to be more intensive.