1. Fixed.
2. Hm. Gray area. The "avoid unnecessary directional prefixes" directive conflicts with the standard directional prefix treatment for a named road overlap. In the case of a road name changing like this, I'd probably use the departing road's name. According to the MilepointRoute2015 shapfiles, the Lake St -> West Lake St switchover happens at Carrier St. WestLakeSt_W? Yecch. But online maps are consistent about a switchover at Swan Lake Rd, and FWIW Google lists addresses on the Carrier<->Swan Lake section as vanilla Lake St. I dunno man. Confusing enough that I'll just go no-build...
3. NY55 points relabeled. Added NMainSt, named for the South/North switchover here, instead of multiplex (_N) style labeling. I'm open to quibbling about the validity of the label; what exactly a "non-essential direction specifier" is was never clearly defined...
4. South Hill is an adjacent geographical feature. Relabeled SouHillRd.
5. Turns into S Mountain Rd farther south. Relabeled in both files.
6. Relabeled in both files.
https://github.com/TravelMapping/HighwayData/pull/2741