The Better Investment? Skipping the 50mm f/1.8 II and getting 40mm and 50mm f/1.4?

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I am new to photography (well, took two classes of it during the past school year as a highschool freshman), and plan on buying my first lens. (Poor 18-55mm kit lens seems like it isn't going to last long.)

I need-ahem-want to get a "Nifty-Fifty", and I've heard/read/watched/seen countless praise and glory for the 50mm f/1.8. But, even more acclaim for the f/1.4 (and expectedly, more for their L lens sibling).

Since I'm just a kid and have no money to get the f/1.2L (and I'd rather get the 24mm f/3.5L tilt shift as my first REALLY piggy bank murdering L lens), I've juggled on the idea of either getting the inexpensive 50mm f/1.8, or chuck a little more money and get the f/1.4. I really rather not have duplicate lenses of the same focal length.

I also plan on getting that adorable pancake 40mm, in both cases. I really would like to own both 40 and 50. (I could get a 35mm f/2, but I'm not sure about that)

My thing is, I would surely will not be able to buy lenses in immediately after each other, so that means I would be stuck with one lens for a while before being able to buy another lens.

So what's the better investment? (Yes, it's a rather tight, "Either this or That" option; a perfect world would let me choose freely Q.Q)

1. Buy the 50mm f/1.8 and be stuck with it for a while before being able to buy another lens. (Either a zoom/telephoto, or the 40mm)
2. Buy the 40mm f/2.8 and be stuck with it for a while before being able to buy the 50mm f/1.4. (And get a zoom/telephoto after that)

My idea of how my first set of lenses (through my high school years) would go:

1. Kit Lens (Hopefully would last long enough)
2. A Standard, Short Focal Length, Prime Lens (50/40)
3. Telephoto/Zoom Lens (I would get 70-200mm f/4L as my first L lens, but using one those without an image stabilizer with my hands only good for Blair Witch Trial movies is NOT a good idea for me)
4. A wide angle
5. My dream lens, a tilt-shift.

I could get other lenses as I get older (I know I'll continue my love for Photography), especially a Fisheye (I use a Ø58mm Fisheye Adapter) and a Macro (I use extension tubes, albeit ones without electronics), but I believe they aren't as important to what I plan to do as of yet.
 
1) Owning your first three lenses all within 10mm of one another in focal length sounds pretty silly... So certainly not a 40 and a 50 prime.

2) Primes aren't THAT much better than 3x zooms simply by merit of being primes. It has more to do with them being able to be offered at wider apertures, etc. for less money due to engineering reasons than straight up amaaaaaazing image quality or anything (maybe 25-30% higher IQ in the 50 1.8 than in your kit lens, for example, which won't matter in most normal print sizes and situations). So I'm not even sure you want to necessarily go for a mid range prime at all as your next lens, unless slow apertures are the #1 bottleneck currently in the kind of photography you like to do.

3) Also, I suggest not purchasing lenses on how they look. What is it about the 40mm STM that you actually think would be useful, aside from it being adorable (it is adorable, for what it's worth)? And what makes you think the kit lens "won't last long?" Hopefully you're using it for taking pictures, not hammering nails. I still have mine without anything at all wrong with it after like 4 years, and only recently stopped using it. Presumably you're just saying this because it is plastic, but I have never ever heard of anybody breaking a plastic lens mount.

4) What exactly do you like to shoot the most? This should be determining your lens choice more than anything else. I'm not sure how you can have a list of the exact order of things you want to buy for the next 30 years in order, before you even have the experience with them to know what you like...


So first, answer #4. What kinds of photography excite you the most? Not which type of lenses. Then we can go from there, and make pretty much any one kind of photography work for you with one new lens on a budget. Do you want to shoot at night more easily? Do you like portraits? Do you like landscapes? Architecture? Macro? Wildlife?
 
I would skip buying the Iffy-Fifty, and just buying an actual GOOD lens; either the 40, or the 50/1.4. The 50/1.2-L is overrated in many respects; you can get a better lens optically in a Sigma 50/1.4, for less money. I used to own the Iffy-Fifty. I gave it to my wife's nephew after I had bought the 50/1.4, which is a very good 50mm lens.

The 40 is a cute little lens; I do not own it. My only current pancake is a Nikon 45/2.8 P-Nikkor, which is a fine manual focus lens. The 40 would have a nice angle of view on an APS-C Canon body; although it might not seem like it, 10mm in difference in the shorter lens ranges makes for a completely different lens; a 50mm and a 58mm lkens for example, are decidedly different focal lengths on full-frame, as are 40 and 50 on APS-C.

The 40 is cute, no doubt. It's also an f/2.8 lens. Which is what it is.

A better thought would be 35/2, 50/1.4, 85/1.8. Those three focal lengths are very handy to own, for a lot of things.
 
5. My dream lens, a tilt-shift.
Also, there are a ton of options for getting one of these at the same cost as a normal lens. If that's your "dream" why not get that first?

An Arsat 80mm f/2.8 costs $430, 1/3 of a Canon.
A lensbaby Edge 80 (tilt only, no shift) optic + a composer body to put it in = about $450, also 1/3 of a Canon.
A random decent old Pentacon 6 lens + a tilt shift adapter to EOS = probably like $260, 1/5 of a Canon.
I made my own for $150 that works fine.
These guys: MIREX-Adapter für die besondere Fotografie sell tilt shift adapters for mamiya and some other lens types to Canon for $400 or so.
 

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