MacBook Pro 13" vs 15" vs iMac + Macbook Air?

So, my Late-2011 15" Macbook Pro has finally run its course and I'm in need of a new computer.
Unfortunately, I'm not sure exactly where to start. I like a lot of the bells and whistles because I'm on my computer a lot, but I'm not sure how many of them I actually use, so I was hoping that I could get some advice about which set up is the most practical for my needs but gives a lot of bang for the buck.
I am both a writer and a current education major about to go into student teaching. As such I will be doing a lot of presentations and papers and will probably use Word and Internet the most on my computer. I also multitask A LOT, so it's pretty important that my computer is able to keep open five different apps with one of them being Chrome with 8 tabs open. I also have my entire iTunes library on my computer because I listen to music and audiobooks a lot and I also watch TV pretty frequently on my computer. I do some minor video editing for class as well as picture editing for fun.
I must have some amount of portability so I can take my laptop to class with me (we're required to have Apple laptops in my education class) but I really didn't mind carrying around the 15" Pro. Weight's not a huge issue for me. I also like to have portability so I can hang out with my roommates down in the living room and do homework with them. However, I also like a pretty good amount of storage so that I can store all of my word documents (and I have tons) as well as my presentations, my iTunes library, and my substantial picture and video libraries as well.
I want to have this computer for upwards of 4-5 years, so to some extent I'd like to have it future proof and really reliable.
With that said, I've come up with some options that I think might meet my needs.
1.) 15" Macbook Pro Retina: 2.5 GHz Quad Core; 256 GB Flash Storage; 16 GB RAM
2.) 15" Macbook Pro Retina: 2.2 GHz Quad Core; 512 GB Flash Storage; 16 GB RAM
3.) 13" Macbook Pro Retina: 2.8 GHz Dual Core; 512 GB Flash Storage; 8 GB RAM
4.) 13" Macbook Pro Retina: 2.8 GHz Dual Core; 512 GB Flash Storage; 16 GB RAM
5.) 21" iMac: 2.7 GHz Quad Core; 1 TB Fusion Storage; 8 GB RAM (AND) 11" Macbook Air: 1.4 GHz Dual Core; 128 GB Flash Storage; 4 GB RAM
So, yeah, which one is the most cost effective to meet my requirements?

Hey There amyenne22,
There certainly are a lot of options for your computing needs ... based on your requirements above, I'd like to offer a few additional suggestions to consider.  I would suggest option 2 above as the 15" MacBook Pro is going to be your primary computer for school/work and the screen you will be looking at the most.  It is also a powerful video editing tool.
I would also suggest keeping your personal "entertainment" - music, photo and video libraries on an external portable drive (with a complete backup on a second local external drive).  This will free up the internal hard drive for your school/work documents.
Regarding option 5 above:  If you have a TV with HDMI, you can use it with an Apple TV to mirror what you see on your computer or iOS device to a larger screen. You really don't need to buy two computers.
Here is some information from our website:
Apple - MacBook Pro with Retina display - Performance
https://www.apple.com/macbook-pro/performance-retina/
Apple TV - AirPlay - Play content from iOS devices on Apple TV.
https://www.apple.com/appletv/airplay/
Storage - All Accessories - Apple Store (U.S.)
http://store.apple.com/us/accessories/all-accessories/storage
That's my personal input for what it's worth ... )
- Judy

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