Is there any shop that I can actually sell a decent amount of stuff to them without them running out of money so fast? I have to travel to like 6 different cities to just cell a few things. Not to count the 25+ Dragon bones and 25+ dragon scales I have in a chest.

I was wondering the same thing, and I'm only level 7. But how else am I supposed to afford my first house if I can't even find anyone to sell my loot to?

Thats where speech perks come in handy

A high Speech skill will let you buy perks to permanently increase the amount of gold merchants have available. So by investing in a shop several times you can insure it always has thousands of gold to buy your items with. Other than that, just wait a day for them to replenish their money.

What are some Easy ways of getting your speech up then? (I am on console)

The only way to increase Speech is to buy and sell a lot and use Persuade as often as possible. But the absolute easiest way? Just find a Speech trainer and pay them. I know there is one in Markath in the inn.

ninja'd