In all of your observations you are very much correct. After doing this work for 20+ years, this is what I have learned: (1) Your Resume is the Projects you have worked on and the tools used in those Projects. Job Titles and who you worked for mean less. Intelligently describing each project you worked on is TruGold in an interview no matter how old it is. (2) Stick with the most widely used tools until you have 3-5 years with each one and then they become secondary (SQL,.NET,JS,XML,CSS,HTML) (3) Go after projects that are most widely sought after with clients (CMS, CRM, LMS, eCom, SEO) (4) If the project is worthy, do whatever it takes to be part of that project solo or on a team. (5) Certifications and Degrees are more important for Gov work only. (6) Create a tool that websites will use (e.g. Sitewide bad url checker) by doing this you automatically convey to clients that you understand the engine for the wrench you just created. The sky is the limit in this field, what you invest is what you will get out of it.
Over 20 years I have been "mousing" for 8 hours a day and I firmly believe the only thing that saved me is using a big honking trackball from Kensington
As one who has used Adobe Reader since 3.0, it really is hard to comprehend why this product continues to advance in complexity. Are there strong numbers of users out there really using the advance features of Adobe X?