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You should have a 301 redirect setup so that everything goes to one address, ie. www.jeremygower.com....so that no matter if they type index.html or www.jeremygower.com/ or jeremygower.com it all goes to the same place. Other than that, an easier method (and you should probably do both...just put a canonical tag on that page, then no matter what the main page will get the link juice.
And yes, it probably will - either way, you should fix it.
Please take it for what it is, advice from a wannabe SEO. I'm basically a newbie at it, but here's what I think:
Use directories, not sub-domains. Sub-domains basically tell google to separate everything. They work well for people that have user generated content, like wordpress.com because if one user posts horrible dupe content with pages of links it doesn't hurt the whole site. On the other side of things, that subdomain does not get favoritism from google because it's on wordpress.com...
So, for your site, I'd recommend against sub-domains. It's pretty, but it doesn't bode well SEO-wise.
Also, dont forget to 301 those domains to the appropriate URL when you change things up 
Well the canonical will be different for every page...so if your page is:
www.jeremygower.com/contact/index.php
your canonical would be:
Basically, what that says is..."hey google, it doesn't matter what URL you think you're at, make sure that the only one in your search engine is the one in the canonical tag"...therefore, be very careful with it as well. If you simply put www.jeremygower.com as the canonical for every page, google would de-index every other page of your site.
Anywhere in the head is good.
IMO, unlimited ends up being a bad thing...the way those things work is that godaddy (or whoever) puts a ton of websites on the same server, so think about the 500 or so other sites with 'unlimited' bandwidth using your server. It makes it slow...for instance there's about 400 domains on the same server as my domain, and yes, it's slow a lot of the time...the cheap plan on a small orange I'm sure is similar but I'd expect better quality than godaddy. (they dont have unlimited)
I have no idea about outsourcing...but I have no training in graphics and little experience and was able to create a pretty decent infographic. This was back in March and I'm still seeing tremendous traffic from it today. It's also the highest pagerank page we have, and it gets about 4x the traffic of our homepage. However, I'm not sure about your niche, but I have found that nobody is converting to sales. It drives a lot of traffic which is great, but I'm not sure we've gotten 1 lead from the traffic it has generated. Not sure how to fix that, but thought I'd put that idea in your head.
Also, you asked about tools...I used Illustrator and Photoshop. Illustrator is a pain to get started with but look for some tutorials for graphs online and you'll find some pretty easy to make graphs that look really nice.
If you're not at all graphic minded, I'd look for someone on odesk.com to do the work for you. As it will take quite a bit of time if you want it to look good, and the graphics programs you need will be costly if you don't already have them like I did.
OSE is not 'live' data...it's archived data. What you are seeing is the web as it (mostly) was as of the beginning of May. Next update scheduled for May 29.
I can only tell you about our experience...we had the same server (in house) for probably 5-6 years, then we moved in January to an off-site host. I paid close attention to the rankings because I was actually wanting to see an increase because the new server provided faster load times. With the exception of normal fluctuations, we saw no change in rankings from the switch.
Campaigns > Settings > Go to bottom and delete (or archive it so you can get the data later!)
Subdomain will receive less authority because example.com/omaha will receive some benefit from being in the parent domain. Are you saying you want to get rid of the domains that have been in place for several years? What are you wanting to accomplish by switching these sites?
I agree with Russ. I've used many rank checkers and they're either weekly (seomoz) and work pretty well, or they're daily/hourly and are not reliable. I remember finding SEscout and was very pumped...until 2 days later when I looked at the charts...it would show us as rank1-5, for a few hours, then drop off the map, then at 300, then back to 1-5...it just wasn't reliable at all and confused the heck out of me when trying to analyze anything. So, I decided to build my own program that I was planning on releasing as a service, but I'm reconsidering...still building it, though. Anyway, it works brilliantly which is much more than I can say about...pretty well everything else. If you have the resources, build your own Custom = Best.
I believe that bold/strong has minimal effect at best. USE HEADER TAGS! I haven't heard anything specific to what you're asking, but I'd venture to guess that Google will see font-weight:bold the same way they see <bold>tags. They are smart and I'm sure they've put in methods of accounting for the probably millions of sites that use things like (assuming that works, not sure).</bold>
Short story: I wouldn't worry about it, unless you can find direct evidence to the contrary. But, for goodness sake, use header tags!
When I built my rank tracker I was originally going to get 50 per page, then noticed the results are much different from 10 results per page. That was at the beginning of March - not sure about before that time.
Why do they have to be H1?
Anyway...Matt Cutts says no CSS hiding!
Well, they're all going to be at different locations, going through different routes to get to your site. It can also make a difference what is the load on your server at the time. I like to use one that allow for multiple URLs like
http://seobyindia.com/tools/website_speed_test.php (just found on google, couldn't find the one i've used in the past)
This way you can get a good picture by doing 10 tests in a row...average them then there ya go. I had to do this when we moved servers to get an idea of the speed increase we received.
I'm all about the keywords at the front of the title, I think it helps CTR as well. One thing I will say is that you should expect a decline in placement when the titles first change. I've changed the title of our sites before and it always hurts at first. Of course, your results may vary - but if not, resist the urge to go back and just stick it out.
I get it, just not sure that it's 'ok' to do...anytime you're hiding something, it cant be good right? Anyway, I'd do something like:
<code># <img< span="">src="whatever.jpg" alt="whatever" /></img<></code>
That should work right? At least, I think it's your best bet. I will say that I do have competitors that do what you are wanting to do and some are higher than me in rankings, so...your call, but I wouldn't.
Well, 301 would be best...but I suppose in that situation what I'd do is use the canonical tags...but that's a pain as you'd need to do it for like every page...
In short, that's just whack...I'd find a new host.
Edit: P.S. Why can't yahoo just die already?
Be sure to check out opensiteexplorer.com, and not just the SEOmoz site...at the moment (because the update was yesterday), opensiteexplorer.com has more fresh info...for whatever reason the SEOmoz site lags behind.
The drop in rankings could be just because you changed the titles. For some reason google doesn't like it when you change titles, perhaps because it signals them that you're trying to change them in order to rank?
Anyhow, I've changed titles on one of our home pages twice in the last 3 or so months. I wish I would have just left it alone...each time my rankings dropped, then started to climb. I'm basically where I was to begin with now before I changed anything and I'm leaving it alone now!
Anyhow, I'd make one more change to get rid of most of the duplicates and then leave it alone. That said, I like:
Upload Name - tag, tag - Brand (fileid)
Well, you aren't supposed to have a business address that customers can't visit, so no...plus those photographers with home addresses shouldn't have their home address listed unless they actually operate their business from there (studio in their home). From the Google Places Quality guidelines:
Do not create a listing or place your pin marker at a location where the business does not physically exist. P.O. Boxes are not considered accurate physical locations. If you operate from a location but receive mail at a mail box there, please list your physical address in Address Line 1, and put your mail box or suite number in Address Line 2.
http://support.google.com/places/bin/answer.py?hl=en&answer=107528&topic=1656880&ctx=topic
I used to do on-location photography and listed my home address for a while. Google called me to verify it and asked some questions regarding if people could actually visit it. I gave answers like 'I occasionally do photography there'. He acted annoyed but let it go.
Personally, it's only helped me as it's knocked down a couple of truly horrible backlink spammers in my niche...but I still think Penguin is bull. I should not be able to hurt competitors, period. And for all of those that say "A good backlink profile will trump the bad links"...that may be true for Amazon and SEOmoz, but for the Barbecue Restaurant in a Pop. 20k town on the interstate, it can mean disaster. It's bad enough with all of the fake reviews going around, but add in the fact that 20 bucks can get your competitor 20k bad links compared to their 5 good ones, it's going to make a huge difference.
Search engines cannot should not operate like this. They should be moving forward instead of backward, it's simply not fair to the real businesses that try to do good. They need to focus on rewarding the good instead of punishing the bad. Heck, regardless of fairness that's just good operant conditioning technique. Anyway, there's got to be a better way...
We moved up 2 places this morning for the main keyword for our niche (number 11, gah so close to first page!).
Personally, I think the way you have categories set up is good, broken down by broad category (ie. finance). Though I'm not sure that 9 to 5 type jobs fits in with that. There's got to be a category that each of those jobs could fit in. Overall, I think that the categories you're using works out well for your site. The way I think of tags is like free keywords that do not need text around them...more specifically for your site, for the ob/gyn article I'd use the tags: obstetricics, gynecology, ob/gyn, medical.
One category per industry...so category=medical, which would include doctors, pa's, nurses, medical billing, etc.
Get the Yoast SEO plugin and in the settings there's an option to no-index the tag pages. Do that and it'll solve the duplicate content issue. For me it's more about user experience...I personally like and use tag clouds when browsing.
IMO, people worry too much about 'how many keywords', etc. I like to design for the user, then go back after I create the page and figure out if I've used enough keywords...as far as tags go I wouldn't worry about what you're using the title and just make it natural, but that's just me.
Also, I'm not sure if you're making $ from the site yet or not, but I'd look at getting another host. Your site is kind of slow from where I'm at and people bounce fast these days.