Aha, You have definitely given us the guts on seals and bearings there Kody.
Did you hear about the baby seal that walked into a club?

A point we all need to consider is that with all or most machinery, bearings are a sacrificial item. The machine will continue to function efficiently without damage to the rest of the machine provided the bearings are replaced at predetermined intervals. Fsst, glug, glug.
So the big question for us LYers is "What is the predetermined interval?".
The question can not be answered without further information such as, type and quality of bearing used, environment, budget and desired perfomance. Glug.
This creates what might be called a spectrum, one end of which might be, "When the wheel won't turn any more I'll replace the bearings.", and the other end might be, "I want to win these races, so I wil replace the bearings between each race.". Glug,glug.
A sealed bearing will have more drag and TEND to keep out foreign particles longer and therefore give reasonable performance and TEND to last longer. I have had new $35 stainless sealed bearings spoiled by ingress of foreign particles on their first use and had $3 steel sealed bearings withstand 6 months of heavy use before contamination.
Further, when the grease in a stainless bearing is replaced with light oil there is a tendency of the metal to spawling as happens between a 316 stainless nut when screwed onto a 316 stainless bolt under load.
A single side shielded bearing supplied with total loss lubrication from the unshielded side will have minimal drag and not be contaminated due to the washing effect of the lubricant. Impossible or impractical to achieve a constant supply of lubricant with a land yacht, but possible to supply sufficient for a race of short duration by half filling the cavity between the bearings prior to each race. Fsst, slurp. R&C.

Another good thing you mentioned is hub caps. I have seen this done on a LY by using silicon adhesive to attach a plastic cap from an oil container or similar to the wheel over the axle end and nut without touching them. By doing this, with a single side sealed inner bearing and open outer bearing (both with grease washed out), the cavity between bearings half filled with light oil, there should be sufficient lubricant for a whole race meeting. An added benefit is the reduced drag of the seal (from the Bearing Straights) caused by the gradual egress of the lubricant from the tween bearing cavity. Slurp Ahh.
But it is like you say Kody, if it is fun and with your family, fantastic, if not why bother??
P.S. When "Cisco" the yacht is at Rosslyn Bay, she will have aboard the ingredients for "Sombreros" and you can sail her all the way to Keppell and back. Cheers Cisco.