And if you try to cross the border from Crimea to Ukraine, the Ukrainian side will not ask you if you "want to enter Ukraine". They consider Crimea to be Ukrainian, so they'll treat you as somebody who is already on Ukrainian territory, just passing through an internal checkpoint. Which means that you must have had entered Ukraine legally before, and then traveled from there to Crimea, and back. If you try to enter Crimea from Russia, and then from there to Ukraine, then as far as Ukraine is concerned, you have committed an illegal entry at the moment you entered Crimea without going through a legitimate border checkpoint - so they'll just arrest you for that.
Furthermore, if you try to enter Ukraine at any other border crossing, but they have evidence that you have previously entered Crimea from Russia, they will also treat that as a past illegal entry.
This is true.
A few years ago I flew from Moscow to Simferopol (Crimea) and was advised that to not visit Ukraine in the future, for risk of arrest at the border. I'm not sure how Ukrainian border authorities would know of my visit to Crimea, since there is no record of it in my Australian passport, but I would not want to take the risk.
Don't limit the the definition and use of (navigational) maps by minimizing the "fuzzy feelings" created by (political) maps. Your hypothetical doesn't work, who goes to some contested territory and then wonder where they'll end up in jail or when they'll fall on a military checkpoint? Most of these areas are not ideal for foreign tourists. If you want a map to navigate immediately around Yemen, Syria, Morocco, northern India, Aceh, South Sudan etc you're in trouble.
Entire countries with nationalistic pride and a populist/authoritarian leader like China, Russia, Pakistan, India, Morocco... fight tooth and nails to have maps that conform to their world-representation. Because they can suppress speech and justify violence against populations usually in these territories or manufacture causes for military confrontations. That's usually what political maps are for and they matter if you're a tech company.
Maps are usually supposed to represent aspects of reality, in particular those relevant to moving around and understanding places (e.g. whether someone will stop and check your passport, or which country's laws you should consult in a particular location to minimise your chances of getting thrown in a dungeon). I get that many people get fuzzy feelings from looking at pictures that look like maps but instead represent a hypothetical reality they would prefer to be in, but there must be a better term for those than "maps".