Hey Mary, as you may recall I have a toe issue that is now over a year old and STILL not better. Anywho, my ortho told me that it was critical to stretch my calf muscles daily. I have already been diagnosed with a condition of hyper mobility in my joints and my ligaments are actually over stretchy, but he still encourages me to stretch the calves for the toe issue. My old martial arts instructor (who is a certified Feldenkrais teacher) is also a huge fan of rolling your feet on a tennis ball, so I'd say your onto something there.
Like Roger, I have monkey toes and often pick up things (clothes, pens, dog toys, etc) from the floor either because I am lazy or just to see if I actually can pick it up. My Dad always called me monkey toes because of that and the fact I often curl my toes under my feet when my feet are sitting flat on the floor when I'm in a chair. Best of luck to you!!
Oh, one more thing, I just remembered a dancers stretch that may help you. Sit on the floor with your legs extended. Pull the tops of your feet back as far as you can towards your chest (just using your leg and foot muscles) with your toes extended/relaxed. Then extend the ball of your foot out and down towards the floor as far as you can (your foot should look as if you were standing on just the balls of your feet, like you use to peek up over something too tall). Leaving your feet where they are, now point your toes to the floor. Now pretend your are picking something up with your toes (your toes should curl down and under your feet if you can) and pull the tops of your feet back towards your chest and relax your toes. You are now back where you started. Eventually it becomes a nice fluid motion. I usually just do ten or so once a day, but I'm sure you could do more/less and change the frequency to suit you.
I have NO idea if how I described it is helpful, but it is a fairly common dancer stretch. I would search for a youtube video for you, but I can't look at videos on the work computer. Let me know if you need more clarification.