Research is absolutely hard to get into when you're not in a university setting! As someone who is not at University anymore, I struggle with the same things. So you are definitely not alone!

Learning to evaluate sources is a skill, like any other. It will eventually come naturally with more practice and expertise. Assuming you know the basics of evaluating sources (publisher, author's credentials, peer reviews, etc), your next skill to develop is identifying and analyzing literature reviews. These are the sections of books (and sometimes articles) that explain the literature that has come before. A good literature review should discuss the shortcomings of that work, and why they felt the need to write something new. It should also give you an idea of how academic thinking has evolved on the topic. You might also get good reading recommendations out of it!

For example:

Historian A says that King SoAndSo of Fictionia was a bad King because of his poor tax policies, losses in wars, and reputation for lechery.

This may remain the dominant argument, and literature following this argument goes on to examine individual aspects of this argument in smaller pieces to either confirm or deny this position. Nearly all of these will reference Historian A.

Historian B comes along some time later, saying that while King SoAndSo of Fictionia certainly wasn't ideal, he had good priorities, and fell short in that he was advised poorly. They may use documentary evidence not considered by the previous author, or there may even be newly-discovered documentary evidence.

Commence historians taking the new dispute to articles and perhaps even further books as they hash out the details even further. All will reference Historian B, but acknowledge the positions of Historian A.

Historian C enters the game in the present-day, dissatisfied with the current state of affairs, and presents a new theory, that King SoAndSo may have been well-intentioned, but was warned several times about his advisors, and should have followed contemporary social norms by getting rid of them at the behest of his subjects.

Academia argues again...

Being able to form a rough timeline of how arguments changed, who is being referenced by nearly all other sources, what names you see coming up over and over. This will help you establish the main views or arguments on a given topic and a rough timeline for how scholarship has evolved. Now, you don't need to go back to 1950 and read old scholarship. In fact, I usually work backwards a little bit when I'm first getting into a topic. But you'll develop your own flow as you go along.

The most important thing is to not be discouraged! There really is no wrong way to start. There are certainly ways that are easier. But start with something that is broad enough that you can read it easily, and use footnotes/endnotes/in-text citations to narrow your studies down when you find something that makes you say "tell me more..."

You are also always welcome to ask about a source here if you aren't sure, or if you're dubious about an author. Those questions are often easier to answer, and are often good for SASQ threads. You may be slightly more likely to get an answer to "Is Historian C's book about King SoAndSo academically sound?" than "How did King SoAndSo's tax policy affect Fictionia in the long-term?" because they are often quicker and easier to answer. You can also see if there is a Flair on the sub in roughly your area who has an open DM policy. Some may also have a recommended reading list in their profile!

I'm sure my colleagues will have plenty more to say, but I hope this helps for now!

Edit: Correcting SASA to SASQ

I have previously answered As historians how do you find sources and put them into context when writing a book?