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Matilda was named heir to Henry I, as his direct descendant, and Stephen swore to uphold her claim just like the other Barons. There was no actual bar to her rule, either. Much of the problem was Matilda wasn't particularly likable and her husband, though quite capable, was an Angevin. Anjou and Normandy were traditional enemies, so it was hard to hold a coalition together.

Steven was relatively weak and known to be petulant. In my opinion, they were both terrible choices for ruler.

It's not entirely clear whether Steven was motivated by ambition or pressure from other nobles. Motives like that are hard to gage. We do know the Henry I got them all to swear. We definitely know that as soon as the old guy kicked off, they split into factions. Stephen had more support and geographic advantage and got himself crowned.

Barron-wise, some guys supported Steven because they were against Angevin rule, some because having a woman in charge worried them, some because of the money, some because she was haughty and generally unpleasant, some because he'd make a decent puppet. Some Barrons supported Matilda for their oaths, some because she was the Granddaughter of a stunningly good king (He probably murdered his brother to get there, but he did a first rate job while in charge), some for money, some because Geoffrey was a very good war leader, some because they were Angevin.

The only reason the war stopped was Steven's son Eustace got killed. It was dead obvious at that point that Geoffrey and Matilda-fitzEmpress' son Henry would be King in a few years regardless. Steven was old and sick from the endless war. Matilda's side knew she was too unpopular to really rule, so they made a peace treaty agreeing to stop fighting with the understanding it would be Henry II, not Matilda I.