What strategies might you recommend for selling items throughout Skyrim?

I am a thief/smith and I generally have kept the majority of goods I loot. But now I've been thinking of turning over a new leaf and becoming a traveling supplier for merchants. I have a vast array of goods to sell but I find it difficult because most other merchants only have between 750 septims and perhaps a few thousand. Some merchants even have as little as 50!

Any thoughts on best practices in this regard?

I downloaded a mod to increase most merchant's gold stores to around 2000, which I find makes for much easier selling. There's also a 10000 gold version, but even my liberal suspension of disbelief wasn't going to go that far. Still, every gamer has their preferences. Anyway, http://www.skyrimnexus.com/downloads/file.php?id=769

After all 4 city influence quests for the Thieve's Guild, fences will have 4000 gold, minimum.

there are perks in the speech tree that increase merchants' gold.