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I would take the new sites and recreate the posts with identical information.  I would then redirect each old website posts permanently to the new posts on the new website.  I think you would lose a lot of link juice if you were just to redirect to a homepage.

Google adwords tool is a great tool, but you can also use the competition keyword analysis tool to see how hard it would be to obtain those rankings.  There are also sites like wordtracker.com which can also assist.

I think you can use it in your title, but I would only pick one.  I would probably use the city first in my title

"Chicago Car Loans | Website Name"

"Atlanta Used Cars | Website Name"

In your body text I would also include variations of these keywords to keep things honest.  you want to write content for your users and you keep your SEO inline with that.

Honestly I think there is way too much going on the page.  I find the layout hard to follow. I would like to see an image-slider with nice crisp photos and text below it.  Also I think you need to integrate a more clear and defined call to action to your website.

I agree - when adding 'alt tags' it is essential to describe the image and not stuff for keywords.  Typically I will work my keyword into my description if it doesn't look spammy.  For example, If I am working on a fence companies website and they have a page dedicated to "city fence"  I will make the alt tag "privacy 'city' fence |  6ft pickets " or something to that extent.

I agree with Tom.  Backlinks can be from anywhere as long as they don't appear to be blatant spam.  I tend to agree that a backlink serves a greater purpose than just link juice and may actually send relevant traffic and business to your company.  I would try to target as many local links as possible, but branching out to a global mindset won't hurt at all.

I disagree I believe there are some authoritative directory links, but they have to be high quality.  Yahoo directory, BOTW, Dmoz (etc).  Make sure that the page your site is going to have a high enough page authority to match the editorial price point though.

It really depends on what kind of site your friend's site is?  Is it relevant to your business niche?  How many links does the site point out to?  I think it looks a little unnatural for it to always link exactly to the page title.  I prefer one link from one root domain and I try to aim for it not to be in the footer.  Can't really say if its going to hurt your SEO effort - only trial and error will let you know

I have noticed when i add meta keywords in my websites for keywords im targeting bing comes back around and ranks my site's quite high.  I know a lot of people say "if i use meta keywords then my competitors know what I'm trying to target"  Who cares just do what you do and keep building quality content and authority and you will be perfect.

one thing to keep in mind is server down time and server speed.  A lot of websites can be affected by having a slow host or the website being deindexed for significant downtime.  I have a client right now that is on network solutions and had his site deindexed because it was down for 5 days because of a unix environment issue.  The website is still taking 8-12 seconds to load and is killing his traffic.  We are in the process of moving it now ;).

I would keep them as do follow and just brand with your company name.  Don't use any keywords such as web design.  You will not be penalized for a branding anchor text of your company name, unless your company names is 'shoes' and at that point why would you need to do any seo work

I would consider this spam.  If you are ranking number one for a keyword and someone visits and leaves your site without a conversion, there was a reason for it.   Dominating multiple spots might sound like a great idea, but it is going to be hard to formulate unique content when you are targeting such similars keywords.  I would rebuild my original content to reflect multiple variances of the keyword and make sure that page is super authoritative and try to rank naturally.

I believe Google is against paid directories that accept everyone.  Directories such as Yahoo, BOTW etc charge a fee, but those fees can be considered an editorial fee.  Believe it or not high quality directories actually do reject applicants.

In google's guidelines it tells you to submit to directories, but people ended up taking that and submitting their site to thousands of directory sites not matter the quality.  Submit to the big high quality directories and you will be fine.  Make sure that the directory page you are submitting to has a higher page authority that way you can pass some link juice.  These are my personal practices and beliefs and may vary with other people on this site.

Another great idea for receiving backlinks is to become a "sponsor" for a charity or host local meetup meetings online.  If you can get your company noticed for donating to charity or sponsoring an event you will get massive backlinks just through news articles and stuff like that.

Here is my opinion on each of the items you are in:

I am not a fan of directory submissions.

3-5 guest posts is a good idea as long as the site you are submitting to has a lot of traffic and isn't super spammy with other guests posts.

I am a fan of local business directories - it will help you in your local footprint and will allow you to build some authoritative links.

Forum and signature backlinks are abused and overused.  The only time I would actually consider using this is if the forum site actually provide you leads (For example, a business message board, marketing forum, business community)

Squidoo Lens are now No Follow and also contain a ton of spam.  I think you would be better of building a blog on your website and building original content there.

I still think there is value in blog commenting as long as you are providing diverse anchor text and valuable non spam links.

Im sure it is possible it could devalue down the road, but Title, URL and Body are one of the easiest ways to identify if the content is relevant.  Google also takes in account bounce rate so if 'title', 'url' and 'body' are targeting 'shoes', but your website is about garage install it will be able to tell immediately that your site is not relevant.

Well in today realm of SEO - you are really hiring a strategist that obtains high quality backlinks instead of low quality links in mass.  You can definitely hire a company that is reputable to work on your website and provide some great value.  I don't think it would be wise to hand it off to someone who has no SEO experience and is just doing a checklist everyday.  Just my thoughts though.

I would personally would hire a full time SEO consultant.  I wouldn't want that company doing SEO for me and definitely don't like what they are offering.  They say there method is Google Penguin accepted, but its super spammy.  Eventually it will be caught by Google and you will be left in a worse place.

I guess the main thing to think about is....

if they are not automating this process how in the world is it worth for them to supply all those links, articles etc for that price point each month?  If its not automated then its definitely contracted out overseas.

As long as your server is located in the country your business is located I think you are fine.  I would find it odd if in the Google's Algorithm it weights server location with any significance.  Although I could also see that having a foreign hosting location could have an impact on Google.

Your category pages should be no-indexed if they don't have rich unique content per category. It is hard to say without seeing the category pages if it will provide duplicate content, but in most cases it will.  You should also no index your archive area as well because that will definitely provide duplicate content.