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New to photography and have found myself wrapped up in it, what an exciting and fun art form!
I have a Canon Rebel T6 (1300D) that came with the standard kit lens as well as a 75-300 lens that came as a package.

My interests are really in people - photographing people's seasons of life wither it be engagement sessions, weddings, newborns, etc. I absolutely love photographs with a shallow depth of field, I love bokeh, and I love taking shots outside.

Here's my question - I am ready to purchase a lens on it's own, I just don't know where to start with all the conflicting information you find online. I would love to purchase the nifty fifty, however with my cropped sensor I know it will act more like a 75mm lens and that seems to present some issues with shooting, for examples, newborns inside their home.
I really don't know where to start here and would love some advice - keeping in mind that I'm a beginner and would like to keep the budget reasonable.

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.

This goes against my instinct to straight-up recommend a lens, but I just did a quick faceted search on the B&H website:
Prime lens, less than $300, Canon EOS...
I came up with: Canon EF-S 35mm f/2.8 Macro IS STM Lens.

You get a max aperture of f/2.8, a reasonable angle of view on your crop-sensor camera, and maybe the nicest feature... macro capability of 1:1 magnification with 5.1" minimum focus distance.

NB: I don't shoot Canon and have no idea how this lens performs, but it has been said that "it is difficult to buy a bad macro lens".

Edit: I forgot to mention... See if you can rent the lens to try it out for yourself.

Some/most of these points are covered by Hueco, though my perspective is slightly different. Hueco appears to advise going with primes, but I'm a bit more deferential to zooms.

Analyze your current focal length usage.

A lens that covers your favorite focal lengths is more likely to get more use. However, if the reason you don't use certain focal lengths is because of problems with your current lenses, you may want to consider getting a more suitable lens to cover those focal lengths.

Prime vs Zoom?

Zooms:

• Convenient. You don't have to switch lenses (as often) to switch focal lengths.




• Larger and heavier.




• Slower apertures. Few zooms are faster than F2.8. Most are slower than F3.5.




• Weak focal lengths. Most zooms are weaker at the short or long end.




• Cost?

Primes:

• Can reduce your need for a gym membership. Since you can't twist a ring to recompose an image, you'll have to run around a lot more or carry more lenses to swap out.




• Usually smaller and lighter. But not if you're carrying too many of them.




• May have an edge in image quality. Of course it depends on the specific lens.




• Can make you miss shots – If you are caught swapping lenses. You need to think ahead to what focal lengths you will need. (No need for those brain training games.)

"Character" and "Vintage" Lenses

Lenses differ in sharpness, color, contrast, glare/flare resistance, and bokeh appearance. If you are not after absolute image "quality", but are seeking a particular "character", you may consider "vintage" lenses. They often have variable sharpness, subdued colors, reduced contrast, and reduced glare/flare resistance. Bokeh is often quite good though.

If you are after absolute image "quality" as seen in various metrics, "vintage" lenses are not for you.

Your choices for the EF/EF-S mount will be limited mainly to M42, Nikon F, and Tamron Adaptall. You will also need to use manual focus, which isn't easy with the focusing screen, but doable in live view. There are also adapters with autofocus confirm.

How are your current lenses limiting you?

The next lens you should purchase will be largely determined by what you want to do with it.

• If you don't like swapping lenses between 18-55 and 75-300, consider 18-135mm or 18-200mm. But understand you'll likely be sacrificing some sharpness.




• If you want faster apertures to shoot in low light or to increase background blur, you can go to primes or you can go to a faster zoom, like 24-70/2.8 or 24-35/2.




• If you don't mind switching lenses, but find that the 75-300 is too heavy, you can get a telephoto prime to supplement the 18-55.




• If you don't mind the 75-300, but are limited by the 18-55 somehow, you can replace the 18-55 with a set of primes. For instance, 28/35/50 would make a reasonable set.




• If you want a wider field of view than the 18-55 can provide, you can get an even wider zoom or prime.

Some options to Consider

This list is nowhere near exhaustive.

• 28mm prime – Good focal length for group photos. Street photography? I don't use mine much, and wouldn't recommend it unless you really like this focal length.



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  35mm prime – "Normal" focal length on crop sensor. It is arguably the most useful focal length, and you can try lenses with different characters. Bubble bokeh, swirly bokeh, sonnar-like bokeh... This is a fun focal length to play with, but tends to cost much more than 50mm.

  
  
  

  Yongnuo makes an inexpensive 35/2. I don't know what quirks you should expect because I haven't used it.

  
  


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  50mm prime - Some of the sharpest lenses are nifty fifties. This is the normal focal length on full frame. I rarely use mine (50/1.4, 50/1.7) because they are "too close" on crop sensor.

  
  
  

  I also don't like 40mm because it's also too close on crop sensor.

  
  


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  EF-S 18-135/3.5-5.6 IS USM – You may be able to carry around only one lens. Pretty sharp, but aperture is similar to the 18-55 kits.

  
  
  

  The EF-S 18-105/4L IS USM is faster at the long end. The EF 24-70/2.8L USM is faster, but doesn't have as much zoom. It's also expensive and lacks image stabilization.

  
  



• Vivitar Series-1 28-90mm f/2.8-3.5. Inexpensive. Reasonably sharp. Reasonably good color and contrast. Fast F2.8 aperture at the wide end. Minimum focus distance is less than 10 cm. Nice bokeh. Its main disadvantages are image stabilization and autofocus are driven by external biologic sensors and motors (aka manual focus). Look for one with a Nikon F mount to use with an adapter.

A 35mm F1.8

fairly cheap, lightweight and a big aperture

the 35mm starts getting you closer to things, rather than just zooming, meaning that you engage with the subject a lot more.

and I haven't even mentioned that great feeling of getting those 'juicy' depth of field photos