Which MacBook Pro do I need? Retina v. non-retina and how much memory?

Hey guys,
I'm completely lost. I need a new laptop, I'm thinking a MacBook Pro (though this is flexible). I'd like to keep the price as low as possible but still get everything I need. $2,000 or under is ideal.

I'm planning on designing and running websites (e-commerce), and doing graphic design using Adobe and maybe other programs. I tend to save large quantities of photos and large graphic files, so I did crash the hard drive on my old mac. I want to make sure I get a bit more than I need so that it will last a long time and adapt to anything I might decide to start doing.

Of these options, what's the most important?

First of all, retina or non-retina? Non retina can save some money, so perhaps I should choose that with the better processor?

i5 or i7? Any real difference?

256GB or 512GB?

8GB (the max for a non-retina) or a retina with 16GB?

Any input is appreciated! I'm completely tech illiterate and have no one to ask.. :/

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