my two cents on the matter is that the swap is worth it. I did it a while ago, the trannies (two of them) were $100 for both, plus an extra $350 for the adapter gear to the 3spd xfer, drive shafts, bolts, shifter, gaskets, back up switch, etc, etc. However, this was with two incomplete trannies that a regular user of this board promised to send me the rest of the parts for. Thanks alot jeff, still waiting for that nose cone, shifter, and fork! I only did this swap because my 3spd was shot and barely worked anymore. I only used the 3spd xfer because I did not have a 4spd case and the transition gear + bearing was only $70. Kept the vacuum and dash shift controls. The driveline shop lengthened my shift linkage for $10, 3.5".
The 4spd is more like an older car transmission, not a truck tranny, so you would be pleased with it on road. It shifts well, but when you retain your 3spd cased you will be mating an old, worn out gear with a newer, relatively unused gear. This will cause a little more noise, and for on road purposes, probably not worth the effort to retain. If I was to do it again, I would plunk down the $600 for the H41 for romantic value, or tour the junk yards for a NV4500. H55s are way too ovepriced in my opinion. but hell, it's only money, right?