I sail single-handed quite a lot and have set the boat up so that in theory I can reef single-handed whilst afloat. Frank Dye achieved extraordinary cruising distances singlehanded so it demonstrably can be done.
However, I would have some cautions. I have never actually tried out my reefing system whilst sailing alone, and I don’t really want to. In any dinghy, even one as big and stable as a Wayfarer, it will be much better to have one person helming and controlling the boat whilst a second person can set the reefs; this also applies for anchoring, rigging and de-rigging afloat, and even just digging out that bar of chocolate that you can’t quite put your hands on.
One interesting question is how would do singlehanders go to the toilet whilst under way 🙂
Also, whilst singlehanding is great fun, I lack the necessary weight to ever get the boat fully powered up, so I spend a lot of time either spilling wind or going sideways…. which probably means I should have reefed down more. A heavier person than me might get more satisfactory performance from the boat.
On the inflatable, I also sail a yacht and never tow anything anywhere (well, if it was less than about five miles I would consider it) because of the loss of performance. On a Wayfarer there is the added problem of the reduced size between tug and tow, which could cause interesting control problems.
I would have thought that there were two ways around the problem- use the inflatable as it was intended, stowing it between uses, or secondly do what most people do and use the Wayfarer itself as as a dinghy. You might want to consider altering your anchor setup so that you can set up a running mooring. This will probably work out much easier than trying to carry an inflatable.