A good place to start is in analyzing your current shots. Between your two zooms, you've got 18-300mm available. Where do you spend most of your time?

You say you like bokeh. Bokeh is a byproduct of subject/background separation and a decently open aperture for the focal length. Common portrait lenses are anywhere from 50mm to 135mm and f/1.2 and up a few stops.

I'm glad you noticed that you're on a crop sensor and what that does to angle of view, as that will impact your decision.

The next step is in figuring out whether or not you can live without a zoom.

Decent, fast primes come pretty cheap. The pancakes (24mm f/2.8 and 40mm f/2.8) offer a great lens for the money (IMO), the 50 f/1.8 as well, and the 85 f/1.8 on top of that.

However, if you want the normal zoom with a faster, constant aperture...you'll notice that the 24-70 f/2.8, f/4, and 24-105 f/4 are all much, much pricier.

You should never let your gear outpace your skills. Generally, until you can describe exactly why your current gear is inadequate, you shouldn't purchase something new. This is because new gear doesn't make you a better photographer. But, it will open some doors, if you know where they are (it's tough to shoot at night with available light for example without better than f/2.8. But if you're not shooting at night...you wouldn't know that).

So, the best advice I can personally give you is to figure out where you spend the most time given your current set up and buy a prime with a much wider aperture in that range, whether it's the 24/40/50/85. Buy it used if possible. Use it and only it for awhile to see how you feel about it. Then, make your next move.