Just for reference, I have been using manual Lionel brand 027 switches for years with no major problems. Some years ago, I went with the more modern MPC-era designed switches because of the horizontal swinging switch lever. It is quite easy to operate these using nylon fishing line: I call them a poor man's automatic switch track. But this also has the advantage of not having to re-wire the switches from operating on track power (the biggest drawback of the automatic 027 switch) to secondary power. Or having the constant buzzing of the non-derailing feature as the train goes through the switches.
Now there are things you can do to make any switch track more problematic: Having them placed on curves, or directly off curved tracks, or on a "S" shaped section of track. While these may be layout design no-no's, I find many 027 track users do these things trying to optimize operation in a small space, which is my situation.
So I find myself making adjustments to my trains. For example, engines like my K-Line Alco FA's, S-2's and Budd cars, I place a spring over the guide pin that goes into the curved slot in the engine frame... the spring goes between the motor truck and the bottom of the sheet metal frame.
I also replace the loose rivet mounting of truck sets on rolling stock with a truss screw and a lock nut. Legend has it this was done so that the trucks could be turned inward with the coupler beneath the train car when boxed up. But as is, these loose mountings of the trucks with rivets allow for a good deal of wobble... a serious problem when backing up a train through 027 curves or through a switch track, especially with the fast angle wheel sets that want to ride upward over the rail with all the weight of the other train cars, and force being placed on the couplers, when being backed up.
Occasionally I have had to use needle nosed pliers to bend the end point of a swivel frog on the switch, so it makes better contact with the curved rail of the switch.
The other thing also is that I run smaller sized, shorter length train cars and engines that are clearly made and designed for 027 curves.
So not to brag, but I haven't a derailment in many, many years, outside of my own error, like forgetting to throw a switch track. Or if a particular truck derails, I know the problem is the truck. On a modern rolling stock truck, probably the gauge of one of the wheel sets does not match the other wheel set on the same truck. On postwar trucks, they may need some lubrication. With locomotives, since I stick with types of locomotives that are similar, I know if a single loco gives me a problem on a switch track, the problem is with the loco and not the switch track.
TrainCzar, the first thing that struck me is you are running items that Lionel cataloged as "0" gauge items, not 027. So while they may make it around the 027 curves, they'd be much more suited to the wider radius of 031 curves.
Given your comment about Lionel 042 switches, one thing I've noticed that over the years, roller pickups have gotten a little wider from some other makers. Maybe not a problem for you given the couple of products you mentioned. So while these wider roller pickups may insure better electrical contact, it can also cause shorting on operating tracks and switches. Some of the later K-Line rolling stock came with a wider pickup that gave me trouble, so I swapped out the pickups with a narrower type and the problems stopped. Also have you noticed that on some postwar locos, especially steamers, the roller pickups are pretty narrow.
Just my experience here.