So, let's say the guy selling the skipjack were to lower the price by 33% which would make it a whole lot more attractive...
Obviously a cheap boat has issues and needs stuff fixed, replaced, and upgraded and that costs money and that can get seriously nuts. For instance, it's a given that the sails need replacing as well as the running and standing rigging which will run more than what the boat cost new. All of a sudden that cheap fixer-upper is starting to look real expensive.
A sensible approach to such a dilemma is to put a simpler rig on the boat and dispense with all the stuff you don't actually need because the less you need the less it costs.
Now, I've made no secret that my favorite rig is the balanced lug rig because it is the most bang for the buck. In case you're hazy about what it looks like, here a picture of Tad Robert's Harry 2...
Right away we can see there's NO STANDING RIGGING. That's a huge cost savings as there's no wire/turnbuckles/staloks/tangs/chainplates or other expensive rigging bits... Better yet, there is a lot less to fail so it's safer. There's also a lot less running rigging as a halyard and a sheet is all you really need.
This rig also does not need a lot in the way of expensive deck hardware either. No big winches or vangs (the rig is self-vanging) so you're saving money there as well.
The downsides are you'll have to build your own masts which is actually pretty easy but a great number of folks have a fear/phobia of spar building. It's a bit of a head trip for some folks and, as it is a different rig, there is a bit of a learning curve when it comes to actually sailing it.
Just about all of the above can be said for the junk rig which is really the same rig just one that's evolved a little differently and has a lot more running rigging in the mix.
Me, I'm all for the whole less-is-more thing so the western balanced lug makes the most sense to me.
The two books I find indispensable for converting a classic plastic boat to lug rig are "The Chinese Sailing Rig - Design and Build Your Own Junk Rig" by Eric Van Loan and "Practical Junk Rig" by H. G. Hasler and J. K. McLeod. Another couple of needful books that will earn their keep are Thomas Colvin's "Sailmaking: Making Chinese and other sails : Sailing Chinese Junks and Junk-rigged vessels" and "The Sailmaker's Apprentice" by Emiliano Marino.