I didn't mind the Sam bits. It just kind solidified his character as its always been, pretty basic. He's just a simple man trying to do the right thing(which yeah, can be boring). I don't think they can make him overly complicated until Bucky gets his shit together, which then helps Sam get his shit together as things get worse for him.. otherwise it'd actually be bad writing because too much too quick/busy. There is definitely going to be some sort of plot device where they essentially need one another for a common point.
He does mentioned that he has 6? contracts lined up via the military and we saw one, which he tries to put up as leverage for the loan. As well as mentioning the whole in good faith thing, more than likely getting free shit by using his "prestige" in which the dude didn't even really recognize him. I feel its trying to serve up a few things, that just because hes a hero; he ain't getting free real estate. The blip has caused economic problems. And that the funding of heroes is now in question for the viewers, as it was never really a thought prior. I'm pretty sure they're going to tee-off something about how the US Govt doesn't trust him either. Iirc, he had his original wings stolen for him, then had them stolen for him again in Civil War. During Civil War, he was on the opposite side of the Govt. It's also only been 5mo after the blip? As far as tech, after it taking damage, hes showing repairing it.. and I believe his last tech was from Stark who is no longer. But true, why doesn't he just call up Potts for a favor, but maybe shes stuck in legal because us govt(armor wars?). I also think SHIELD was the primary government funding toward super heroes until it went to shit via Hydra, and I guess Stark takes over in the funding department.
I couldn't really imagine Stark really had a conventional hourly or even a salary. I doubt he would have paid any of the avengers other than in Stark tech, or the room/board in the Avengers compound.. I think there is a nod to that, where Tony says he pays and designs everything to make everyone look cool in Avengers. And I could be wrong, but isn't his whole shtick essentially egotistical? I just can't see it, him paying out abunch of people who he is shown hating on in different situations.
I also don't think he's broke per say, but at least in my experience.. doing the whole charter boat thing is expensive, esp with lack of clientele. I live by the coast and have known Captains and worked deckhand on some charter boats and that shit is live or die in terms of financial fluctuation. I forgot who was saying it, but it was someone within Marvel i'm pretty sure.. went on to talk about things like, how post blip, the concept of being gone for 5 years only to return to a house that is no longer yours and occupied by strangers, a few other examples I can't remember. /shrug I'm just diggin.
Either way, I think they're just trying to world build cause/effect of the blip. And from my understanding the series is basically going to play the whole, Sam is in the shadows of the greater heroes and having to somehow prove himself as an equal/worthy of the shield. More than likely bring out some of the race card cus muh discriminations, and the US Govt isn't going to want him rocking the Capt American mantle. I think its safe to say their recipe is pretty much most our questions will get answered some how, but doesn't mean it will be good/liked.. just more that its their point of conversation.