Wonder if I should get a smaller play bike! 
Yes you should 
But then I have to get a trailer, and kit and the list goes on!
Only once, then it is all sorted.
And also possible to get a road legal small play bike, but I prefer to trailer.
Road legal like?
I was thinking 125cc 2 stroke or max 25cc 2 stroke.
Maybe a bit small

A number of 250 and 450 4T's can be made road legal and road kit installed.
Having said that, I only made my 450 road legal since it is a requirement for the West Cost Baja (not the Baja Light).
I prefer to trailer my play bikes to where I want to play, not adding km's which are not part of the fun.
It does mean extra expense but it is a once off and the "trouble" of trailering is minimal (IMHO anyway).
Look at Rough Riders KDX200 in the For Sale section, he really looks after his bikes and that KDX for R15K is a great deal in my opinion.
Then add R6K to R8K for a secondhand trailer and you can get started.
The riding gear (Helmet, Boots, Body Armour etc.) you would need anyway.