For me, the choice of gear always starts with getting inspired. I see a style of photography I want to emulate and then I figure out what gear will help me achieve it.
Here's what I have found...
1. The most important tool is software. I use Lightroom and Photoshop. Lynda and other sites have great tutorials. Magazine tutorials can be helpful too.
2. Light is the most important resource. Anything that will create (speedlights), optimize (ISO, big apertures), or channel light (reflectors, diffusers, locations etc.) has the pottential to dramatically improve your photos.
3. Some of my favorite photographers get their style from knowing how to use their gear toward a certain effect. I could get a Leica and Noctilux 0.95 lens, but my shots might still lack the style I'm going for.
My suggestion would be to go through Flickr and 500px, pick out 20-30 photos that you want to emulate and then use those to make some purchase decisions.
I apologize for being pushy and off-topic, but this approach will put you further down the road to some great shots.