A funny and creative approach to the 'overruled and unimaginative' universe of the trekkies is How Much For Just The Planet? by Peter David.
After this book the 'big bosses' in the Star Trek merchandising empire forbid any further 'experiments' in that direction. Which in itself tells us enough.
Is this canon? Who cares. It's Star Trek, the original series, in book form. And it is outright fun. Kirk is, well, Kirk. The Klingons have a chip on their shoulders (and bones on their foreheads). And the sellers are selling their planet. Sort of.
You may be hard pressed to find a copy these days. It's listed on Amazon, and though I think the price is a bit steep it is a nice read...