Towing is
definitely a tough concern as is the weight issue. If the weight is too much for you to physically manage, then the
sacrifice of power makes sense. But that means you need to spend some time picking the right smaller motor too. Like I mentioned before, my 4-stroke 5 hp only weighs 3 pounds less than my 2-stroke 9.8 hp.
The first thing I would suggest is that you get one of the easy lift motor totes (
http://www.defender.com/product.jsp?path=-1|215570|294|443923&id=98948). This will put a handle on the top of the motor that will make it easier to handle. One of you can be on the boat with a rope attached to the handle to help the other lift and control the motor. Try this out over land first to see if it is doable.
It might still be too much weight and then the answer is to go for a smaller motor. There are many cruisers that only carry small motors or carry two motors because of the weight issue. I remember talking to one woman who loved her 2.5 hp outboard because it meant she didn't have to weight for her husband to put the motor on. She could just jump in the dinghy and go whenever she wanted.
If you choose to sell I would put an ad on Craigslist advertising you motor for sail but that you would consider a trade for a smaller motor. At the very least you should be able to trade your motor for a smaller one straight up. But you might actually end up with a couple of dollars extra when your done. I highly recommend the Tohatsu/Nissan 2-strokes as those seem to give you the best power to weight ratio.
As far as towing with the motor on, we only do it for very short trips in protected areas. I have seen dinghies flip with the motor on and sometimes you may not have the motor when you flip it back. Even if you do, now you have to quickly clean and oil it to not end up with a boat anchor. However, as you pointed out charter companies send boats out with motors towing behind all the time. When we chartered in the BVIs, we towed with the motor on everywhere. I never even considered taking the motor off. But then again, I didn't own it and wouldn't have to deal with the submerged motor.
We've been considering the Dinghy-Tow system for our inflatable (
http://dinghy-tow.com/). One of the advantages it that for a lot of the cruising we do, you could leave the motor on. My wife could easily launch and retrieve the boat by herself with this system.
Good luck and fair winds,
Jesse