A well described post.
With so much experience in Print and design, it will give you a 'leg-up' in many facets of web design.
There is a growing push in the industry to be friendlier to mobiles or 'mobile first' design, and a push away from the 'Photoshop' first types of designs that have perpetrated the web for the past 15 years. This means that a greater emphasis on content and layout using optimized C.S.S. and proper semantic structures.
As such I recommend you first familiarize yourself with 'mobile first' design and proper semantics in modern web design. Once you get a solid understanding of these, it should be time to learn HTML and CSS. It is best to start with HTML 4.4 an not drop right into HTML5 (as it is a semantic mess being so young), however it is ok to look into CSS3, although most of your CSS work will be with CSS2.
CMS do serve an important role, however please know that there is needs that go well beyond what CMS's are best at doing. Also you may be asked to convert a 'standard non-CMS' site to a CMS template so you shouldn't skip learning the craft. Also CMS's are overkill for many customers. Of note, out of the last 5 CMS customers (who paid substantially more than static sites) for their described need of 'self management', even with extensive training, not one of them manages the CMS themselves, they instead ask me to do updates for them. What is increasing clear to me, is that most customers don't understand the web, the terminology, the rules dictating traffic draw, or fequency, that their sites fail to meet their expectations unless I have made sure that they do the things they need to, on a successful schedule.
I actually have one customer that I converted their manual site that I performed regular updates to each week to a CMS and they have received and paid for 100 hours of training between 3 staff assigned to this project. After one year they still send all updates to me and ask me to update the manual site. I have asked them why they don't move to the CMS that they paid for, and even the Executive Director will say "If we start to use it then the board will expect us to take it over. None of us have the time to really do it regularly enough to get proficient at it, nor can we even carve out the time needed just to do the updates. You are more knoweldgeable, better at Internet Marketing, and even turn our articles into something our members like to read on the Web, so we did the CMS to show the board that we would try, but they now realize that you provide more value than the CMS, so we just leave it as it is".
I am very careful to recommend a cms for any new customer and I am sure to relay these stories and really test their conviction to what will be needed to make it a success.
I have one customer that has successfully taken over the majority work on their site. Although ironically they have hired a full time internal person, who they paid me to train, that all they do is handle the web work, and it costs them almost double per year for their salary versus what I used to charge them. Obviously then need a controller to 'point this out'!
I hope this helps.