A redesign is a good opportunity to evaluate the pages of the site and what they are doing. You will need data for this such as recent Google Analytics data. Any page that you decide to get rid of because of low traffic to the page you will want to redirect to the page above it, or a consolidated page that contains similar information. You can also allow the pages to 404 for a few weeks to let Google know for sure that you have rid the site of them. Depending on how high traffic of a site it is, Google may not be crawling the entire site anyway. With that said, I would not worry about including all 188 pages unless all 188 pages are providing value. A large portion of most websites are doing more harm than good when it comes to SEO because of the low value of the pages. Google looks at that. There is a difference between a site being content rich and content saturated. Hope that makes sense.

There are a lot of options. Building Wordpress sites is where building websites in DreamWeaver was around 2004. Everybody is building Wordpress sites but most are not setting their clients up for success by properly securing the sites, offering SEO that actually produces results, and ongoing support to help them grow.

Would probably look at online learning websites like Udemy.com, download as many audiobooks as I could on the topic and start reading blogs from popular people in the industry.

You could use Woocommerce with their Subscriptions plugin or Easy Digital Downloads with their Subscriptions add-on. Both are pretty solid choices. EDD might be a little lighter weight than Woocommerce but I think Woocommerce has more reporting details and export options for accounting software.

You could probably use any Wordpress theme that had a design and feel you like. I would use a good events plugin such as Calendarize It. That plugin makes it easy to set up a nice calendar of events. You can make specific calendars for each country, category and city. They could view them all on one calendar or filter down to specific locations. You could even enter the venue information for the events as well. It's a pretty decent plugin. You can see an example of it working here: http://tvqma.org/schedule

I have lost passion at least 100 times. It happens and the situation you find yourself in can make it challenging for you to care. I totally get that. If you are planning on getting out, I would try to position yourself so you have some time to regroup. If you are in a position to do so, I would spend the next year reading, traveling, meeting with people, having discussions, sleeping, and thinking. My best ideas have came from times where I walked away from other things that were not working for me any longer. It takes time for our minds to detach from the things that are dragging us down. If you are like me, at that time I was working too much and not giving myself time for growth. Stopping everything and focusing on myself and my family renewed me and allowed me to once again access parts of my mind that were bogged down with everything I had lost interest in. Hope that helps.

I would use social. Since you know your potential users are spending a lot of time on their mobile devices and you need to get them to pay attention to their computer, I would market to them through social. Target the social channels that your target market would be frequenting. Don't be afraid to get creative. Even if your software is B2B, remember that they are people too and are probably on Facebook and Instagram. Take advantage of photo and video. Facebook video ads are still pretty cheap and targeting is great. Our Facebook video ads usually cost us about $0.05 to $0.08 per video play.

I am a pretty big fan of the Sensei plugin from Woothemes that uses Woocommerce. Sensei is a paid plugin but its pretty powerful. You could use it for a content drip on your website and also set up courses. We have set up multiple websites using this plugin including using it to power an online driving school with prerequisites that have to be met before moving on to the next chapter and tests that won't let you proceed unless you get a passing grade.

It depends. Are these screencasts you are wanting to record? On the Mac, I use Quicktime these days as it is included and seems to be more stable than other solutions. You can also record using the camera on your laptop. I am not sure if you can use Quicktime to record both your screen and your camera at the same time. If you are on a PC, I believe Microsoft Expression Encoder 4 can do this.

We run multiple Wordpress Multisites and they are very customizable. Assigning custom domains to a Wordpress site is not supported out of the box, but with a domain mapping plugin, you can do it. We have a multisite deployment with 50 sites running on it and all of the sites have their own domain names. The backend url is even mapped so the client does not have to look at your domain. If you have any other questions, let me know. I have been working with Wordpress Multisite since it was Wordpress MU.