Thanks for the feedback and questions everyone. I will probably do some more of these in the future too.
@hughmac - I am happy to share, but fair warning that I am also not a coder. The code is poorly described, messy, and inefficient, but largely functional for my particular use case. I have thrown it up on GitHub (not that I have any actual git tracking going on locally):
https://github.com/xc-racer3/PDAL-Basemaps@gordhun - I agree with Cristina, that very rarely is importing any OSM data actually worth it. With the number of issues (missing info, misplaced features, over simplified features, etc.), the amount of time it takes to fix those flaws is typically more than it takes to just draw the features yourself. It is a nice data set that makes it impossible to screw up your georeferencing for the map file, but given how nicely georeferenced the rest of my other basemaps were (all nice projections without any weird units) I could just as easily have skipped the OSM step. I put it in for the stream, because it is a good place for new mappers to start.
@Jagge - Thanks for the advice, I will play around with this! I've never played around with using the different returns, so I will need to do some reading and experimenting to get something useful.
@FrankTheTank
1) I am glad the stream was a little bit helpful at least.
2) Yes, this functionality is really nice to have. Use the Line Edit Tool (Keyboard shortuct "L", or the button that looks very similar to the edit button in the top left of the ribbon), select the feature of interest, and then CTRL + Click on a line segment to toggle between curve and straight. For any given tool (editing or drawing), you can always look at the bottom left of the screen to see what you can do with the tool with various keyboard/mouse combinations.
3) Select the two different objects that you are looking to merge (with either the edit or line edit tools), and then click the connect paths button (circle that is 1/4 blue and 3/4 white) midway through the ribbon. I used the keyboard shortcut of "C" in the stream, which is probably why it wasn't clear. This tool takes the two existing ends and averages them to create a new point (deleting both existing points) to connect the objects. You can do the same thing with area symbols as well, using the Unify (Keyboard "U") tool instead (two overlapping yellow circles).