Ultimately that is a question that only you can answer, but there just a couple common considerations that you should at least be aware of before coming to a final conclusion.
In all likelihood unless you have a very simple and straightforward need there are going to be gaps between what your ideal workflow looks like, and the workflow you’d be adopting with an off the shelf software offering. It almost seems like a bit of a cruel trick that the simple workflows are also the ones quickest to roll an in house solution for. The question is whether the gulf that exists between the needs and existing solutions is bigger than the expenditure of time, resources, and opportunities that you’ll be looking at to roll your own.
If there is significant gap between your needs and the existing solutions, but you know that there’s a significant demand to fill the same needs you have, development might net you a new product of your own. That is assuming that you already play in the software market. If you don’t, you once again need to consider the time and expenditures of expanding your offerings into an entirely new category of business.
Do you or the people on your team have the necessary skillset to create your own solution? This doesn't necessarily mean you need to have all the requisite skills and knowledge before starting, but that you need to consider and do the math on whether any skills or knowledge you need to acquire to complete the project fit your needs or professional development plan. If you’re a software developer, or looking to become one it can seem like any programming skill development is a win, but sometimes those skills may be better acquired with a different project, or at a different point in your development timeline.
If your math on the first and second considerations has you leaning towards a custom solution, but your math on the third consideration either rules out or gives you pause on deciding on in house development, do you have a budget and available local partners to outsource development? I say local because regardless of the savings, dealing with someone from a different geographical region is likely to introduce additional headaches into the development project. It can work, but be careful.
If this is the case, the bulk of the decision comes down to whether you’ll get more enjoyment and personal development out of writing your own software than you will working around the limitations in existing options and just getting on with doing whatever the core hobby or personal task is.
There may be other considerations specific to your reality, and some of these might not apply. I just find many people tend to just consider whether an existing option fits perfectly, and whether they have the skills in house. There are a few other things to consider though, and whichever direction you choose there will be opportunities that you give up. Don’t let those hangups stop you though if you know that your new solution will fill a need for others, or if the journey is the most valuable part of the equation for you.