Ive had a CR-10 for a while and I like it a lot, but understand that most printers in the "entry level" price range are going to be a little finicky at first until you get it dialed in. Some have good luck and get one that hits the ground running, others have bad luck and have nothing but problems.. most seem to be somewhere in the middle. Generally speaking, you can be set up and produce decent prints in like less than an hour with most decent printers these days. Its commonly said that if you like to tinker and upgrade, get a Creality, and if you dont, get a Prusa. There's a cost difference there, so budget may dictate, but everyone says Prusas just run like a top right out of the box. My CR-10 ran pretty good from the start, had to make some adjustments here and there.
All that aside, I love 3D printing and being able to draw something up on the fly and print it out on the spot. But understand the limitations of your print material and learn how to design with layer orientation and slicing in mind for best results. Most people start with PLA but I would say start with PLA+ and don't bother with regular PLA unless you are making non-functional cosmetic stuff (like a lot of people do), there's just no point and the cost difference is negligible. Its easy to print and has pretty decent strength for functional stuff. There are better materials out there for sure, but thats a good (and easy, and cheap) place to start.
As for picking a printer, decide if you ever plan to build huge parts and go from there. You can upgrade a lot of parts on most of the common printers, but except for a handful of monetarily impractical situations, you are more or less stuck with the build area of the printer you select - So don't get too small if you plan to print large objects. I have a very large build plate, but I almost never use it anywhere near capacity. I like to print small functional parts most of the time. But that being said, you can always print small parts (or how about 10 small parts) on a large build plate, can't print large ones on a small plate. If you really want to look into the future, you can look into what would be required to print successfully with other materials like ABS, TPU, Nylon, etc and select a printer that you know will be able to grow with you, but thats a pretty daunting task. I would just say get something that will get your feet wet and then IF you decide down the road to print with materials, that your set up can't handle just get another dedicated printer at that time (Or upgrade the snot out of the one you have).
There is a lot of decent free design software out there, Fusion 360 probably being the most popular. Like any Autodesk product, it does some things well and other things are pretty terrible, but ultimately for a free program its pretty decent. I have worked in AutoCAD daily for years so I much prefer that environment, but there are pros and cons to each. There are a bunch of slicers out there, some cost money and some don't. I still use (Free) Cura and haven't seen much need to switch, but there are a lot of options out there.
I think I've rambled on enough, good luck!