Sorry for the delay in getting back to you, Bushie.

I would definitely paint the wood panelling.  

In regard to colour?  I can see two ways.  

1. The whole wall painted the one colour with matt on the plain surface and a semi gloss on the panelling

2. A light semi gloss colour on the boards with a different hue above.

Get the best paint brush you can afford.  They will last for ages and do the job more easily.

For the panelling, consider 2 coats of primer/undercoat for coverage

I think trestles/planks would be the go for your handyman for the cutting in at ceiling height. I suggest doing a wide ceiling cutting in for the whole perimeter. By then the original ceiling cutting in is dry enough for the wide band of wall cutting in.  It can be started at the same point and paint in the same direction.  Then proceed with the roller work.  (while the trestles are rented out to the neighbours who will copy cat your renos)

Oh......and make sure he has his underpants on when he's above eye level.  Otherwise there might be more panting than painting.

DEB