Liz, given the information in your last couple of sentences I think you should hold out for a M31. The 31 Mk 1s are now coming into budget and likely to have self tailing winches and a windlass as standard. The Mk2 sugar scoop is great but could be replicated with a bathing platform on a Mk 1 quite easily. If that means buying on the other side of the country and moving it, well so be it. That is what hired skippers and friends are for.
Fist off some light reading. How about this thread were two old blokes took a M31 from Cardiff to New York
http://cardiffyachtclub.proboards.com/thread/1776/moody-old-blokes. Then post 2 in this thread:
https://www.sailnet.com/forums/boat-review-purchase-forum/8704-moody-31-more-questions.html How did that Moody get to the Caribbean?
In terms of single handing, 5 years ago my wife changed jobs and couldn't get the time off for our annual holidays. So I got a leave pass to go solo sailing for a fortnight. I went from the Solent down to Dartmouth and back stopping in between. Initially I was quite concerned about sailing single handed, especially crossing Lyme Bay as you can't normally see land for some hours in the middle. SWMBO doesn't really sail despite the pair of us having crossed the Channel or down to the West Country regularly for a decade. So I guess I was single handing anyway, but being on your own is an interesting challenge.
After a couple of days I relaxed more even reading a book at sea. This is were the autopilot comes in to take the stress and hard work out of a long trip. Allows you to even cook at sea whilst popping up every couple of minutes to see what is going on. On another solo trip I even managed to spend an afternoon flying the cruising chute down the length western Solent for the first time. Its a big sail and needs quite a bit of foredeck work to set it up then down again because it had a twist before finally flying, but the M31 gave me a nice flat stable deck to do this from. Moving around a harbour isn't a problem solo, the boat is stable and tends to stay were its put a least for a while. Sure the view from the back of the stern cabin looking forward makes it look huge and when antifouling it is huge, but also stable to walk around, good news when we get older.
I think you will find that the M31 is two tonnes heavier than a M27 so will provide a much more stable platform for moving around on, all be it clipped on whilst at sea. In harbour it will also offer much more accommodation for you and occasional guests. This is quite important if you plan on living on board for a while. Its not just the length but height and width which helps avoid that cabin fever feeling.
It is also quite doable to cross to Holland and Belgium which are popular destinations for Moody owners and given a half decent forecast, so no reason why you shouldn't follow a well trodden path from other smaller Moodys over the years.
Want a challenge? a Moody 31 with bilge keels did the Midi canal in 2004. I want to do that in ours, just need to retire first. Ruby Rose on You Tube have just done a great series on the Midi in their Southerly 38.
I think you should go and view the M27 and then blag your way onto a M31 to see the difference. You could also charter one with some friends:
https://www.alba-sailing.co.uk/yachts/true-blue/
Having written the above, I now wonder if I have done the right thing in recommending a M31. If your heart is set on a M27 then ignore the above and let the heart rule. You need that fond "look back" feeling as you row away from your yacht.
Pete