So for me I make a trek to my parents house ~150 miles away a few times a year.

In good weather (and good battery condition), I could maybe skip hitting the chargers all together, or get a little bit of charging at my parents house from a wall outlet.

Unless my parents (or my grandfather that I also visit fairly regularly who lives the same distance in a different direction) installed a better charger at their place... In colder weather (e.g. Christmas), I'd almost definitely need to use a charger while going at least one direction.

The problem is, in both cases, there are like 5-10 charges total (not charging stations, chargers) where as there are like 5-10 gas stations all right next to the interstate each with at least 4 pumps, many with 8+ pumps.

I'm concerned that during peak travel in cold weather (e.g. Christmas time travel), I could easily find myself in a bad situation where I can't get a charger because they're all too far away, broken, or in use. There's just not enough redundancy.

I'm in the market, and the answer is kinda, for non Teslas. I do a road trip up the east coast a few times a year and the Tesla will reliably add about 4 30 minute stops on each half of the trip. A non Tesla also requires four stops, but they could be anywhere from 20 minutes best case to 1 hr plus, depending on the availability and status of the unreliable chargers.

A lucid with 400 miles of true range would probably cut it down to two stops, but I don't have $140k

No, there are very few places like that, and most of the populated places are not at all like that.

I took that to mean “I want to complete my common road trip without charging”

A few weeks ago I did my first road trip requiring charging away from home and it really was painless