gidday Cameronc, henceforth known to me as "The Kid"

,
dont ever let anyone tell you that it cant be done

the only thing that will stop you is your, own imagination, lack of money, lack of determination.

What you really need to do is the research..... get that done and the rest is a breeze

. And do something about understanding steel work n welding, That's fairly easy.
Why.. I was thinking along similar lines recently, as far as I know no one has given it a go yet. In another forum here, peoples were talking bout land yachting across lake Eyre. Your adaptation could be of great help to those who like to have a go at that style, although the now wet lake puts that off for a couple of years yet
Aircraft use a combination of wheels and ski's ... and that works

You talk about sails and rigging, most sailing clubs, have members with boats that they no longer use cluttering up their boat houses, and other individuals have them under their houses or in their garages. They are mostly glad to get rid of them

and can be scavenged for parts

. At very small costs. Place adds in papers.
Give it a go Kid.....have a go at YOUR dream....... Best-o-Luck....Cheers Joe