This sentiment matches mine very closely. I agree with the original posters characterization and identify strongly with his troubles. And as a result, I stopped playing Skylines, and passed over all the DLC. Until recently.
So I'm giving it a try once again with a new way of playing that I think may keep my interest. My tactic might be of use to you,
@RonBurgundy
After watching some YouTubers doing some very good 'painting' in Skylines, my interest was kinda piqued. And then reading some peoples' City Journal threads partly piqued my interest also. The combination of these, however, can potentially create a guideline and a real, specific challenge, as well as a well-defined purpose that propels your gameplay.
Conceptually, the notion of building a city FOR a journal, according to a specific concept, has a lot of potential. Via your city journal concept, you can tailor the direction directly toward your interests. As an example, here's what I'm doing right now:
I am going to treat Skylines as a roleplaying game tool. I am building a city specifically in order to make an effort-post city journal /AAR. I am going to build a city that's set in the SHADOWRUN dystopian sci-fi universe, fully functional and as thematically resonant as possible. It will have names, districts, layouts, landmarks and policies appropriate to the fiction. And once it's reached a point of sufficient development, I'm going to start writing up brief shadowrunner schemes, exploits, and mayhem with the cityscape, disasters, mods and screenshots as a tool.
This provides a very clear vision and objective for my planning and building, subduing my sense of 'pointlessness' that I get from freeform city painting. And the planning adds some challenge too. But I want even more challenge on top of that, so I'm going to do this without infinite funds. I gotta grow this sucker from the ground up. That might not sound so challenging on paper, but in practice it's really hard to have a plan and vision for the city, and then build out the 'scaffolding' and grow it while under budget. You end up needing a lot of guideline roads built, which puts a real strain on the budget. Unlike "hard mode," this creates a financial burden that actually has a purpose, and a payoff.
Hope this idea helps. If it weren't for this crazy scheme, I probably would've never picked up the game again, absent a game-changing DLC. I'm hoping for one that explores poverty and it's side-effects, and other more human elements.