Now, the biggest plothole, here, is that... that measely 750 gold can easily be accumulated in just a single day of wood-chopping! A measely 25 sessions at the wood-cutting block - which, even under Tamriel's expedited passage-of-time system where a day passes by in less than 30 minutes, can still be accumulated within a single sitting - can earn enough to have someone murdered.
Food is so cheap that you can feed yourself for an entire day with just 60 seconds of wood-cutting. Clothes are so cheap that you can save up enough for a "fine" set of clothes can be purchased with just two sessions at the wood-chopping block (40 gold for the clothes, 20 gold for the shoes).
And yet, we have beggars. We have "poor" people who aren't necessarily beggars, yet still can't really afford to go after some bandits for their family heirloom sword without making their wives think that they'll starve. Instead of giving them some gold, perhaps I should give them a wood-cutter's axe. Since that seems to be the biggest barrier for them having nice, comfy lifestyles, then it seems that all they really need is that.
Wood-chopping isn't even the only way you can get rich in a short period of time in this universe, either. That guy in Rorikstead can't be an adventurer because... his family can't "afford" armor or a weapon for him? Hey buddy... go take some of your neighbor's crops! They'll buy them right back from you, even though the crops belong to them to begin with, and they have literally INFINITE gold to give!
What... you want that shiny new ebony battleaxe that the smith is selling? All you need to do is go ot Narzulbur; in just ten short minutes, you can get nearly THREE THOUSAND GOLD with which to buy all the battleaxes and armor you could ever want!
So... it seems that the only reason people should ever starve in this universe... is if they literally go out of their way to refuse to do any work at all. Money is as abundant a resource as air... it literally flows into the world like an everlasting stream with no source and no end. I wish jobs were this easy in the real world.
So, I take no pitty on beggars; it's clearly THEIR fault that they've fallen on "hard times," because there are no hard times for them to fall onto.