This comes from me on a quest to make my own custom fonts for my site, and really wanted to point this out:

In the internet, you gotta make a pixel font manually, and then use a converter to turn it into TTF. But how about those fonts that were drawn by hand, and then you decided to pixelate them?

There aren’t exactly any tools that let you do that to them :T The closest thing I’d found was a pixel font converter, which was quite finicky to set up, but got the job done... even if the result had some weird bumps around.

I’ll try to pass the font through FontSquirrel to see if the weird bits get fixed too, so hopefully I get it nailed down :1

Have any of you had similar experiences with custom font making? Just curious if it’s only happening to me xD

I've made a few fonts before! I'm not sure it would be feasible to automatically convert handwriting to pixels. Because I think there are always some quirks with handwriting that look a little weird if they aren't manually changed. Also, it would be good to use font software that lets you manually kern because I think handwriting is much less likely to look pretty when it's monospaced.

It's going to be a very tedious process no matter what, so try to enjoy it! I've used FontStruct in the past for pixel fonts. I've also used Fontself which is a plugin for Adobe Illustrator and Photoshop. I think Fontself would be easiest if you have access to either of these since you can use drawing software to pixelate it the way you want and then throw it into a font file. The only downside is that this is a paid plugin and they made it a lot more expensive than it used to be.

I'm not sure there even is reliable freeware for fonts that can do everything someone might need it to, unfortunately. But there are definitely lots of methods out there that should hopefully get you pretty close to what you want.