I made it this far on a regular one. I ended up with -1 tracks a few times. Is that expected?

Hey Jack, amazing run! $1081 is a massive score, and losing by such a tight margin to a Baron Takeover is brutal.
To answer your question: yes, going into negative track is actually intentional right now! We noticed it very early in development. It originally stemmed from a quirk in the code—the UI only checks if a company has more than zero track to let you click the 'Build' button. When the backend actually executes the build, it rigorously checks if you have the cash, but it just subtracts the distance from your track inventory without a hard stop at zero. So, if you have 1 track left and build a 2-length segment, it lets you stretch into -1.
We decided to keep it in as a feature rather than 'fixing' it as a bug. The game is already incredibly hard and punishing. Letting players intentionally overextend their supply lines like this adds a fun, slight 'Press Your Luck' element that floats nicely on top of the heavy financial simulation going on underneath. It gives you that one desperate push when you really need it!
Thanks for playing and pushing the limits of the economy!