TheGenerator says:
... If we're going to spend gold to get more people ...
If you spend the (village's?) gold on get more people that counts as 'throwing money at the problem' to (more) safely overcome a threat (as mentioned in the first character creation
post). This won't level you up.
50 Gold is exactly 1000 Silver, so it is precisely what you need to level up, any amount spent from there will stop you from reaching Level 2. You can spend anything you still have from your personal funds (in new gold coins if you want, it is fungible) to recruit, but I don't think you have much.
TheGenerator says:
... I'd rather get some of the baron's guards ...
That might be an option. You would need to play that out, though. You would need to gain their trust --they let those people into the manor and may have been with them, these guys implied that the baron was against you after his meeting (with Nixon?) last night. But 50
Gold coins goes a long way towards buying 'loyalty'... but only the type of loyalty that can be bought, though.
Depending on how you approach it: It would probably take Gold to get them to listen to your proposal, but then come down to a roll or two to see if they come with you or if you 'wasted' that Gold which you can't get back. In that case the Gold is buying you the right to speak. You could also try to persuade them to let you speak, and then use the Gold as an incentive to join you, which has the advantage that you don't (necessarily) lose the Gold if they don't like your offer, but with the difficulty of needing to convince them to not attack you long enough for you to talk to them (and after).
TheGenerator says:
... I think that guy I healed is coming too, right? ...
Correct. He is a true believer and did not appear at all afeared of angry wives.
TheGenerator says:
... I say let's risk going in with just the 5 of us. ...
On a meta level (which is alright) you guys know that you will be able to find a way, whatever you choose. You also know that Leveling Up is better for you in the long run.
You characters, though, would probably be much happier with some help. They don't know that the odds will be 'reasonable' (or that none of this really matters?:).
Olaf and Christian are a fairly safe option, the risk there is that you will have less time, and that you (especially Daryl) will be tired when you get to the action.
Since Daryl ended up here --and had no way of knowing you were coming here-- you can guess that the cages are closer to this side of the valley than Olaf's, so you will have to trek all the way there and back again if you want those two.