Sometime in mid 2013 or 2014 as a junior dev I woke up to a call from my company's CEO. He informed me that the legacy system they use for order processing is down nationwide that nobody can add new orders until it's fixed and that I needed to fix it. I had been working there 6 months and was hired along with a senior dev to begin developing a web app to replace this legacy system. The senior dev had left the company two weeks earlier for a better offer so it was put on me to figure it out. I was very frank with the CEO and told him I didn't know if I could fix it and suggested he try to call the company they hired to create it. I didn't even know where the source code was let alone what the design paradigm was or whether or not there was any documentation. He said he would try figuring out who created it and give them a call and asked "As a developer you shouldn't you be able to fix this?" I just told him it wasn't that simple and left it at that.

I get to work and the CEO has discovered that the company who created the software no longer exists and I tell him he may need to find a company to consult on this if I can find the source code and if I can't find the code he might be screwed.
I found the source code in a random IT shared folder there is no source control, no documentation, no unit tests, no test environment, and it looks like nobody had touched it since 2005 or about 8 years.

Despite being completely unfamiliar with the code and the design paradigm I was able to figure out that they were validating customer addresses against an old Google geocoding API that was shutdown the day before and the lack of response was killing the application. I fixed the issue and warned the CEO before deployment that I wasn't able to test but he said to go ahead and thankfully all went well.

People always say thet you should not quit your job before you have the next job lined up, but what if you plan to do freelance? This is my dilemma.

A bit of context (rant).

My current job is my first official job. Small company, VERY HIGH staff turnover rate. I have been here for 2 and a half years. My commute on a good day is < 20 mins, and money is relatively good.

During the last 6 months, all devs above me resigned, which lead to the system maintenance being passed on to the few devs left. Our biggest system is a legacy system (Windows CE), and new clients are actively signed up and new features requested. The codebase is not even worthy of being called spaghetti, changes break every client, I need to wash my hands every couple of minutes. Seriously, I would rather maintain obfuscated code. It is like a bunch of highschoolers wrote the system, though I think they would have done a better job.

Management is nice and understanding, but the state of the codebase is killing the spirits.

I fill my nights and weekends moonlighting to keep my mind off of the 'daymares' at work. I have never been a team player, and thrive on my own. I have been thinking quiting and going full freelance/contract the last couple of months. Should things not work out, I can always go job hunting (see issue in par. 1)

That satisfying rewrite that results in a major removal of legacy code + the devil's number :3