I'd say that's fairly typical for a newbie lol, I've had shameful "victories" as well and I've certainly had defeats where I have ~500 troops total against a similarly large enemy--it's a learning process all the way lol. And don't mistake that commentary as being from a veteran--I still consider myself a newbie since I've only completed one playthrough thus far.
That depends on what you ambitions are, because you're ultimately trading away your freedom for lifelong obligations that you cannot easily back out of.
Let's assume you have the conventional objective of becoming the founder of a new country and want it to be secure, powerful, and maybe unite all Calradia down the line. If that's your goal, I recommend joining a kingdom that's powerful enough that there's NO homeless clans (because homeless clans get first dibs on captured fiefs--something that'll likely deprive you of gains down the line if you aren't careful) but weak enough that you could reasonably take them on once you've secured a power base. Decent examples might be the three Empire factions since their central locations make them easy targets for their neighbors while the corners they can expand into are desirable places to rule over and use as a base for future independence. For example, if you joined the Western Empire, I'd prioritize moving into Sargot, or Charas, or Quyaz (etc.) and then pushing into that respective cardinal direction to secure your own safe and prosperous corner. If, however, you joined the Vlandians, it'd be much harder to secure a safe corner that isn't in Sturgia or the Nahasa Desert, unless they've been badly beaten up and are willing to give you one of their hinterland cities. In that case, well... it'd be another set of problems. Also note that proximity is weighed heavily in fief vote determinations, with the only thing preventing too much of a snowball being that the more total prosperity a clan has the less favored they are.
Regardless, you'll want a nest egg saved away because fief profitability can vary widely. When you have a fief of your own, the rule of thumb is to have no more than 2-300 stashed Tier 1-4 troops to keep expenses down while making the settlement hard to attack, unless you plan on rebelling or otherwise need a reserve of top tier troops in that city (in which case you need a nest egg, possibly in the millions of denars, just to pay the bills since a huge/expensive army is extremely expensive).
Finally, as a mercenary, you're in an ironic position to befriend possible compatriots. Simply release any noble you capture and their families will come to love you, making it that much easier to poach them to your side should you wish to do that (ideally as an independent ruler).