I'm thinking we should somehow bring Awesomicus under our control. He seems useful. This would be a good one to brainstorm.
Do NOT pawn our phone. It's the most interesting thing we have. If we need to convince someone we come from another world, or show off something strange, what would be better? And I really, really want us to have it when we meet Yagrum Bagarn.
There are plenty of affordable places to crash in and around Seyda Neen, although Seyda Neen is inconveniently far from anywhere interesting. Balmora has few caves within convenient distance, but Caldera has at least one or two nearby that would be perfect, once cleared. It's a safe bet that early-game quest related caves (in any quest line) have been cleared, but others might not be. The Legion can hardly be bothered with every cave of slavers and smugglers, else the trade wouldn't be nearly so lucrative.
Now, this is just a thought, but it's entirely possible that our information-brokering could be used to get a small band of outlaws to do our bidding. Just something to keep in mind, not saying we pursue that. At some point, we must try to get some kind of followers, servants, or subordinates. Perhaps we could make a loyal friend of a slave, finding one willing to be our adventure buddy and then purchasing their freedom.
I must say, I'm not so sure about Light Armor now. Though Medium's a bit out of our price range right now, it does have better prospects for upgrading. We won't be able to get better Light Armor than chitin for a long while, as in vanilla the only thing better is Glass, rare and expensive, and we can't get access to Dark Brotherhood armor until the events of Tribunal get underway, which don't canonically happen until after Dagoth Ur dies. Still, for right now, Chitin's the best we can get and still be able to move well. I just hope we'll have the spare coin to switch to bonemold before we get too invested in Light Armor. This isn't of immediate concern, though.