Re the comfrey, it can self seed, less likely in grass as too much competition. But it's such a useful plant you'd have to be seriously over-run to want to get rid of it - did you see Monty Don making it into a feed for the garden on GW last night? Alternatively there is a sterile form called Bocking 14 which won't set seed, I've bought it from the Organic Garden catalogue as pieces of root.
When the time comes, dig a trial planting hole and leave it to see if it fills up with water, if it's dry winter use your judgement, maybe try a hole in the planned area now it's been raining for a few days...
Yes clay soil is fertile but the nature of the soil makes it lock the nutrients up in it and therefore unavailable to the plants. It needs to be opened up with larger particles - in my garden I've used coarse grit and sand plus compost. Compost/manure alone may just sit and stagnate. Lime applied at the right time will help too.
Ploughing or rotavating clay soil can do more harm than good, timing is important, would be better if you were incorporating the above materials at the same time. I loved my pigs for that, they have really helped open the soil up, manured it and destroyed all roots of rushes. A local smallholder would be grateful of some extra land for their pigs - maybe get them to bung you some sausages or bacon if like my OH you aren't a fan of plain pork, or they're bound to have more than just pigs TBH do a swap for something else, free eggs til you have chooks or maybe they have equipment you need?!
Also might be an idea to offer the land again for grazing once it's all sorted and looking like good pasture, it'll only go back to wilderness and you'll be back to square one!!