Sounds to me as though you should just do it, Jim. Although not trivial, it's also not terribly difficult.
I went for many years without doing the steering box, then finally broke down and did it. Wasn't nearly as bad as I had imagined, and the improvement was huge. (Unfortunately I did change some other things at the same time, so it's not clear exactly how much was due to the box rebuild and how much to other things.)
A few thoughts:
Many of the manuals have the wrong instructions for adjusting the front wheel bearings. That "two flats" stuff is for the birds! "Practical Hints" 6th ed says to tighten the nut until resistance to rotation is felt, then back off one half flat.
Some of the new felt seals are too thick. If you are installing new felts, the safest thing to do is first install the hub without the felt, adjust the nut and mark it's location. Then remove the hub, install the felt, and return the nut to the marked location. (However, the felts I got from TRF in 2009 were not too thick.)
I had a lot of trouble with replacement silentblocs not lasting very long. Seemed like they would always start to deteriorate within a year or two. So I converted to a free-turning brass and steel joint from BFE. Since then, Joe Alexander has come up with a cheaper design using Delrin instead of brass (available through TRF). However, the hard joints are less tolerant of misalignment between the steering box and idler arm; so if you go that way, you may have to pay a little attention to getting them lined up. I think mine still aren't quite right, which is why TS13571L still steers harder than TS39781LO did.
I also upgraded the inner A-arm bushings to Nylatron because the rubber didn't last. BFE no longer carries the Nylatron, but I think it's still available from Revington or Racetorations. Unlike the stock nylon bushings, the Nylatron needs to be reamed after installation. Probably a lot easier to go with the poly bushings available from most suppliers (which AFAIK do not need to be reamed).
Contrary to what the book says, if you have the later split steering column (which you should), the steering box can be removed without removing the front apron. I had to take the engine loose from its mounts and jack it up a bit, but overall I think it was much easier than R&R-ing the apron.
A dial indicator worked best for me when setting the bearing clearance in the steering box. I basically added a shim, measured the end float, then subtracted that thickness of shims. It's also important, IMO, to either have the top cover off, or back off the rocker shaft adjustment while checking the bearing clearance.
You'll need a good, stout Pitman arm puller that fits the "drop arm". It's best IMO if you can remove the worm before trying to remove the arm, so there is no chance of damaging the worm.
Getting the shafts all lined up perfectly is a bit fiddly as they say. Almost every bolt has some clearance, so take all the clamps loose (including the upper column) and get it working smoothly, then snug them back down. If it got stiffer, something moved, so do it again.
At a minimum, I would plan on replacing the peg, bushing and seal in the steering box; all of the A-arm bushings (including the brass/steel ones that have to be reamed after installation), the trunnions and all the grease seals (both boots and rings). Idler arm, upper ball joints and tie rod ends might be reusable if they pass the wiggle test (as Geo outlined). The rubber/plastic steering column bushings probably need replacing, if there is any lateral play at the wheel then replace the felt bushing as well.
The books are a bit confusing (to me anyway), the "anti-rattle" rings 60586 are not used with the split column. However there are some anti-rattles springs on the stator tube that are used with all columns. You will also need (2) 606630 bushings, even though the SPC only lists one of them.
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