Windows or Mac for photography and personal work

Hi,
I'm new to mac and have been a windows users all these years. I'm looking to buy a new Mac for the first time. I have other apple products like Ipad & Iphone too.
I'm working as a IT manager as a main profession. But im a photography hobbist with more interest in landscape photography, travel and family pictures too. I do lot of Photoshop & Lightroom works. I dont earn money for my photography. I do spend a lot of the time in front of my computer online like internet browsing, social media..etc.
I need some advice. The below are my question.
1. What is the best time to buy a new Mac? Should i wait till apple releases their new 2014 models? 
2. When apple releases their new Mac products every year?
3. For my needs do i need to go for 13" MBP or 15" MBP?
4. I shoot lot of pictures every week. Not sure will mac be good option to backup all my pictures from my camera just like a windows PC.
5. Should i buy a cheaper windows PC (i5 with HD IPS display refurb for under $500) mainly for photography work and plus another 13 MBP retina for my regular light work? This will cut down the cost little bit.
6. Should i just buy just one high end version of 15" MBP with i7,16GB & 512SSD for all my personal use ?
7. If i buy a new MBP retina now, will i be able to uprade the SSD later? Does the new 2013 macs support upgrading the hardware?
I would Appreciate your valuable inputs and your time as well.
Thanks in advance,

In order (for the ones I feel I can answer):
1. Buy it when you feel it meets your needs. As an IT manager, I am sure you are aware how futile it is to chase the latest and greatest.
2. No one here can predict when (or ever) Apple will make hardware or software releases. In fact, speculation on those things here is forbidden by the TOU.
3. Matter of preference. Bigger screens are nice I had a 27" iMac and loved it.
4. Backing up on a Mac is seamless (Time Machine). EVERYTHING is backed up. I am cautious so I also make bootable clones in addition to using Time Machine.
5. I would not, but my opinion of "cheap" PCs running Windows is very low.
6. Only you should make that decision. A recommendation here would be just another opinion.
7. Yes. A friend of mine did that using a certified third party manufacturer. I always buy from Apple as I am hardware challenged.
Barry
Edit: about # 7 -Clinton is correct, I am sure. My friend has a non-retina model.
Message was edited by: Barry Hemphill

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