Fractional Rig - Short-Crewing?

[Blackbird]

Can I pick someone's brains...mine's single-celled where sailing is concerned. I am interested in a cheap wooden (1959, 13m, draft 1.7m) motor-sailor but the seller is as clueless as me.

The rig:
Oregon pine mast on tabernacle with 7/8 Bermudan rig.
Fixed running backstays.

Stainless steel standing rigging.

Oregon pine rolling boom.

Polyester running rigging

Full set of sails, all of them used in variable condition.

The pics included one of the keel. Could anyone advise me how demanding the rig will be for someone who is inexperienced but is strong and will put in his apprenticeship. We have to spend some money - don't tell me, lots of money... - refurbishing and could we modernise the rig without sacrificing all our arms and legs.

Thanks, Jay

BTW this forum is brill - better than actually sailing for gaining first-hand experience.