Web Design For A Living

Hello Everyone,

I need some honest help with regards to Web design and earning a living online in general. Please bear with me as this post might end up being a long one however I need to set my goals for 2014 so I need to clear my mind as I'm all over the place at the moment.

I have a strong business background and I have always held down senior jobs etc, however a couple of years ago I decided to start freelancing offering proofreading services. That took off straight away however it wasn't paying enough so I started studying web design as I want to pursue this as a career online. I started obtaining basic jobs with HTML and I eventually obtained better jobs etc.

My current situation is that I have a good freelance contract that provides a good wage coming in designing basic websites for clients using wordpress at the moment aswell as other business related jobs. I freelance full time and my income is stable so I'm not going anywhere and I have another business offering forex courses that has been constantly profitable for 3 years(however I am looking at letting this go if the web design works), however I really want to improve on my capabilities to further increase my income in order to be more comfortable.

I am currently designing a small web business offering websites for clients, landing pages, hosting and a few other web related bits.

My problem is that I was talking to a family member who has been in IT for over 15 years(I believe in software) and when I mentioned what I was looking at doing I got absolutely grilled and I was told that it was a very bad idea.

Basically I was told the following:

There is no money in Web design,development
Wordpress is not the way forward
I need to specialize in one type of web design only
I should only study one topic very well such as HTML or PHP
I can get sued for offering Hosting if it goes wrong
I can get sued for copyright if I was to use a wordpress template
Not to offer ongoing maintenance as this will reduce my productivity and that I will never make any money out of it.

I personally disagree with everything that was said as I believe that I should be able to make a good living out of this as soon as I study more. Basically my plan was to finish my comptia A+ course. Then go through HTML & CSS again through W3 and then go through their entire course range so that I get a good broad understanding of coding. I know I'm not going to be an expert in PHP for example however I should get a good understanding to be able to pursue web development as a full time career.

These are some of my computer capabilities so far:
Comptia A+(Due to qualify in 2 months)
Studied HTML through W3
Studied CSS through W3
Diploma in Photoshop CS6
Studied Indesign CS6
I have very good working knowledge of Wordpress
Currently reading books on SEO

So my questions really are

Do you agree with my thoughts?
I am missing something important
Should i really specialize in one subject such as PHP?
If I was to specialize could I make a living just on that one subject?
Am I aiming at studying too many things?

I'm in my mid 30's however I am pretty good with computers in general and I tend to understand code and it's something that I like to do so I am keen to progress in the online web direction. I'm just a little lost as to the right direction that I should be taking to do this right.

Any help would be greatly appreciated.

Thanks in advance and Happy New Year