After asking questions and reading some answers I'm starting to wonder.
Am I being a fool or just scaring myself?
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I travelled for 5 days in Iceland one winter (December) and managed to go in a day from Reykjavik to Hofn by hired car. Another time I drove to Mivatan during May, so although I haven't completed a loop I've done most of it. The scenery is beautiful. The only thing you should consider you might be delayed due to road blockage (snow, ice) so when you plan your route, give a day or two days extra not to miss your flight from Reykjavik.