Input wanted for an article.

Let's say that your company is considering the purchase of an expensive new application to help in the company's software development. The demo looks great, and the feature list makes it sound perfect for your needs. So your Management arranges for a proof of concept license to find out if the software is worth the hefty investment. The boss comes to you to ask you to be in charge of the PoC project.

I'm aiming to write an article to help developers, devops, and testers determine if a given vendor's application meets the company's needs. The only assumption I'm making is that the software is expensive; if it's cheap, the easy answer is, "Buy a copy for a small team and see what they think." And I'm thinking in terms of development software rather than enterprise tools (e.g. cloud-based backup) though I suspect many of the practices are similar.

Aside: Note that this project is beyond "Decide if we need such a thing." In this scenario, everyone agrees that purchasing a tool is a good idea, and they agree on the baseline requirements. The issue is whether this is the right software for the job.

So, how do you go about it? I'm sure that it's more than "Get a copy and poke at it randomly." How did (or would) you go about designing a PoC project? If you've been involved in such a project in the past (particularly if the purchase wasn't ideal), what advice could someone have given you to help you make a better choice? I want to create a useful guide that applies to any "enterprise-class" purchase.

For example: Do you recommend that the PoC period be based on time (N months) or workload (N transactions)? How do you decide who should be on the PoC team? What's involved in putting together a comprehensive list of requirements (e.g. integrates with OurFavoredDatabase, meets performance goals of X), creating a test suite that exercises what the software dev product does, and evaluating the results? ...and what am I not thinking of, that I should?

Didn't know if i should post this in talk or tech, but my focus is on advice, so i guess this is the place.

I am currently in the process of changing my career to be a web developer. Studied IT a few years ago, dropped out due to finances, and spent the last few years working crappy jobs.

I designated all my spare time towards learning the basics. I'm confident enough in my knowledge of HTML and CSS, know how to use Bootstrap and i'm currently learning the basics of JS. The Udemy course i'm taking will cover NodeJS, jQuery and some more backend next. After that i plan on learning Wordpress and a framework i guess (React/Vue/Angular). Have i missed something here?

My final goal is doing freelance web development. My question is, how plausible is this and what else do you suggest learning to have an easier time finding clients?

Also, how soon do you figure i could start doing some basic work with simple websites (even if it means using Bootstrap / altering Wordpress themes)? My country is rather cheap, so even 500$/month on simple projects will be enough of a reason for me to quit my 9-5.

Guess i'll need a portfolio too though.

Anyways, thanks for reading. Any web devs out there care to offer advice? I'm dedicated to achieving this goal, but i'm somewhat lost still.