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Keywords in URLs definitely help your pages rank better for the keywords you are trying to target.  The more precise your URL is to your keyword the better off you are.  As long as your content is consistent and provides value there shouldn't be any issues with google.

I include an alt tag on every image on my website.  I use the alt tags not for keywords, but a clear description of what the image is trying to portray. The description usually includes a the keyword, but also includes other descriptors as well.

Depends what industry you are in.  I think some industries it is essential for someone to know the location and competition professionally rather then just using the same tactics they would normally use.

I agree with Ricky - I would slowly make all those pages unique in some way.  I still find it beneficial to rank to different city pages as long as they have prime content.  Google will eventually sift its way and find those pages as spam.

I think any natural link is fine as long as its not a gambling, pharmaceutics or porn website.  I would caution to make sure that there isn't any negative SEO going on, but it sounds like you have a self sustaining link building campaign without having to do anything.

If you are going to utilize blog commenting just do it naturally.  When I make blog comments I do not use Anchor Text as my name and I vary my URL from homepage, inner page and social media pages.  I find that a well formulated blog comment can give you so SEO benefit along with some direct traffic to your website.

What I would do is get a phone number from Google Voice and put that on the website.  You can then track the logs on that specific phone number.  You mention you have six phone numbers, why?  Alternatively you can create a landing page with a Google Voice number and use it for your PPC and social media campaigns.

based off what you said I bet you over optimized your site for "lifestyle magazine".  Like Richard said the best way of receiving links is having a magazine that beats your your competitors.  Just to throw it out there people may be more willing to share your website content if the sharing icons weren't so discombobulated at the top.  I would also think about using such a harsh black font color and font size.  Makes it hard to read if someone is reading a longer article.

Might be best to use someone that has specific knowledge of WordPress security to lock your site down. Plugins generally don't catch everything and certainly do not lock you down from further attacks.  There are a few steps that you can take to make sure your site won't be infected through simple scripts and brute force.  If you need a referral for a security guys let me know.