Don't ride it as is, that left hand crank is broken and dangerous.
You say you enjoy riding. Bike maintenance is an essential skill unless you enjoy spending a fortune at the LBS getting minor and easy bike repairs done.
The state of this bike fits into the minor and easy repairs. Most other questions are focusing on the cost to turn it into a premium bike, ...
The problem is I'm worried it will be way more expensive than just
forking out $250
Good that you set a price. Then think about how much value has your time (either in term of lost time, or in investment towards building certain skills).
Let's start with the negative aspects.
I can see easily 3 to 4 weekends spent on fixing the bike.
So much time because ...
I hear they still make things called "books" that contain a wealth of bike repair information, including step-by-step instructions on how to identify what sort of components you have and how to service and repair them. You can also keep them open by your bike work area, they don't run out of power, and don't stop functioning when you spill oil or ...
Define "worth it."
If you're wondering if it's financially worth it, the answer is probably not. It'll probably cost you as much or more to replace the parts that need to be replaced as it would to just buy a new bike. .
If you're wondering if it's worth it as a learning exercise, definitely. If you're going to be doing your own regular maintenance,...
Your bike is a low-end entry level bike from the 2000's. If you want to fix it, good-new parts could add up quickly. So look around for one or more donor bikes of similar vintage and see what you can find.
It is becoming common for most cities to have a "recycle station" at their rubbish dump, where usable stuff can be had for cheap. In mine, ...
The bike looks quite smart from a distance but the cheapest possible no-name components have been used to get this bike into a price category when it was new.
Some of the replacement parts you might need will be cheap, chains from £5, freewheels from £12 etc, but you may end up replacing alot of the components to get it functioning to a good standard.
A more ...
To start off, the crank arm isn't breaking, it's quite definitely already broken.
As to repairs - this bike seems to be what would commonly be called a 'BSO' (Bicycle shaped object). I definitely wouldn't spend anything trying to repair it, and would look to spend the money on a replacement.