Unfortunately for me, the amount of gold does feel cheaty as noted in your description and immersion breaking. It's pretty frstrating and time consuming to stay in character and sell off pricey equipment at what you would consider a fair price just because the merchant doesn't have the cash to immediately buy the item.
Perhaps an alternative concept would be a merchant NPC who only buys stuff at a fixed discount (say for example 10%), does not sell goods to the general public (that is, the MC or his companions), and only trades in legal goods (i.e., no skooma or moon sugar). So when you sell something, you can never buy it back; on the other hand you've got a merchant who has the cash on hand to buy those surplus daedra swords in one fell swoop rather than having to juggle your calendar for x number of days to sell them at a higher price to a merchant who you wonder how many buyers is he going to have for that type of item in the first case.
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Perhaps an alternative concept would be a merchant NPC who only buys stuff at a fixed discount (say for example 10%), does not sell goods to the general public (that is, the MC or his companions), and only trades in legal goods (i.e., no skooma or moon sugar). So when you sell something, you can never buy it back; on the other hand you've got a merchant who has the cash on hand to buy those surplus daedra swords in one fell swoop rather than having to juggle your calendar for x number of days to sell them at a higher price to a merchant who you wonder how many buyers is he going to have for that type of item in the first case.