Hi Bryce,
I would probably start with trying to find out why those features couldn't be dissolved into one feature. If they exactly connect, then maybe the direction of the lines is not matching? Try and symbolize the lines using a Cartographic Line Symbol, with in the Line Properties tab defining a line decoration as an arrow (second of the three options). What do you see?
Another possibility is going into edit mode and examine the feature vertices. Select a feature click Edit Vertices and look at the sketch properties. In case of Z or M do they match?
If you want share a few features and I can have a look at it...
Kind regards,
Xander