Yes, you can drill a hole in the trailing edge. However, you won't be able to just pull on the line to get it started. I have to push the headstock in to get it started, and then I can use the uphaul line. I wrap it over the top of the headstock and along the tiller to a clam cleat. I keep mine up in the slip, because when it's down, wave action works the pintles and gudgeons, and I don't want it weemying out the gudgeons, forcing a replacement.
Note also that I have added a substantial teak block for the headstock in an attempt to stiffen up the works, as the cheap-@$$ riveted spacer tubes loosen up over the years and create play in the headstock.