I have been using Clip Studio Paint (CSP) for 6 years and I personally like it enough to have recommended it to a few people. They have matured a lot over the years; there is a big community built upon the software, where a lot of assets, such as custom brushes, particles and 3D models, are available for free, which are (now) easily managed and installed.
I have personally used it for digital calligraphy, designed diary covers for printing, and anime-style illustrations. I'm not a professional artist and never received training in the fine arts, but it appears that CSP is used by professional artists if you are considering using it in that capacity.
This is a one-time purchase; as an indication, the current copies that I am using are 6 years old and they are up-to-date. The 50% discount is also available to the EX version for $157.50. If you already have the Pro version, you can also upgrade for for the difference between the discounted prices of $121.50.
A 3-month free trial for CSP is available if you are unsure about purchasing a license. Do keep in mind that the current offer expires on 2020-06-23.
IMPORTANT considerations before purchasing
Check the system requirements before purchasing. I'm not sure if this is helpful but including as a reference point: while I did get quite a lot out of my laptop with a 4th-gen mobile i7 (4558U) and 16 GB of RAM running CSP, it struggles a little bit at 2560 x1680 @ 300 dpi in terms of smoothness in drawing/painting (larger brush sizes are more demanding) and canvas operation (rotation, translation, etc.); it's definitely not unworkable, but it can be frustrating to some.
This license is for Mac OR Windows and, if I remember correctly (don't quote me on this), it cannot be transferred to a different OS after the initial activation. Also, this is NOT applicable to the subscription-based iOS version.
You will most likely want to invest in a drawing tablet if you are going want to draw and/or handwrite anything. If you don't already have one and are not working on a Windows-based tablet, take the additional cost into account before purchasing a CSP license.
IMPORTANT information about POTENTIAL discounts in the future
Disclaimer: This is just information base on discounts in previous years, I obviously cannot guarantee that those sales will happen.
If you can wait or need to think about it, there will likely be another sale or two before the end of the year. Of note is that there may be a bigger sale closer to the end of the year base on past years.
If I remember correctly the upgrade from Pro to EX has also always been on sale at the same time, so you can also purchase the Pro version now if you and think about the upgrade to EX later if you like it enough.
A note on Pro vs. EX
They seem to have changed their features page such that the comparison between Pro and EX are not immediately clear now. From memory the more important features in EX are (please double check if you're going to purchase the EX version):
- Animations are not limited to 24 frames
- Page management
- Photo to line + tone (manga style) conversion
I hope that helps!
Edit: typos
have you tried krita? how does it compare?