(+) well, a lot of people, even if it's no longer every man of relevant age
The military cannot occupy the entire space of the US so maintaining order of a tyrannical government would require a low ratio of military guards to citizens. With even 50% of the citizens potentially armed and willing to fight back, it's an untenable position for the government.
A militia could fight just as effectively as the Taliban against the government and be several orders of magnitude larger. The US military is good at eliminating identified enemies, but it's pretty terrible at nation building and that's even in its strongest state.
Perhaps a successful militia requires significant financial and logistical backing from nation states, in addition to being well trained.
Do you really believe that the 20,000 to 60,000 estimated [1] militia members in the US is what is defending you agains government overreach? There are more than 1.2 million people in the US army (with a $600 billion budget) and 120,000 federal police officers [2].
Another point to consider: democracies outside the US, that don't have 'well-trained militia of free people', seem to be doing just fine. In a number of metrics that you can consider as a proxy for government overreach the US is actually doing much worse than average: number of people shot by the police, number of people imprisoned, number of (innocent) people executed.
[1] https://en.wikipedia.org/wiki/Militia_organizations_in_the_U... [2] https://en.wikipedia.org/wiki/Law_enforcement_in_the_United_...
Every colonised and now forgotten group of people had what they thought was a genuine well trained militia, for all the good it did them.
If citizens of any country get to make a claim about the effectiveness of an armed citizenry, then it is the Americans.
Those militants are not ragtag. They all receive state sponsorship in the form of finances, hardware, training and logistics.
Your analysis also ignores the reality of asymmetric warfare, in particular the asymmetry of the value placed on the lives of the combatants on the different sides.
Terrorist organizations are far more willing to sacrifice their combatants than the US is, and they have a pool of people who share this outlook to recruit from, which is why they persist.
In the event of an internal armed conflict within a developed country, all sides are likely to value the lives of their fighters similarly.
Reference to: The constitution of no authority by Lysander Spooner, and, The law by F.Bastiat