When can I expect to start making decent money?

Exactly.

My first boss always told fresh grads that he expected 3 years out of them. Year 1 they would be learning a lot, year 2 they would be performing at a good level, year three they would be paying back year 1. He was a great boss and mentor (I still get his advice 20 years later) so I don’t think it is an unreasonable expectation in his case. I do think at least 2 years is good for your first job, unless there is some other circumstance (family issue, toxic workplace, dream job falls in your lap). If you do leave before 2 years I would be prepared to stay longer at your next job. In SF it is not uncommon to move around ever 18-24 months, but in the rest of the country when a hiring manager sees a resume that has a string of 18 month jobs it is a red flag. The amount of cost in terms of money and time that goes into recruiting someone is enormous.

Depending on how strategic minded your current boss is and the level of your performance (we haven’t seen your work), a $5k raise might strategically make a lot more sense to him than the cost of recruiting a new person if you can explain how it will benefit him and make life a lot easier for you. I’d only do this if you plan to stay awhile. If you do get a raise and then leave within 6 months it would not be nice.

I’ve only had 3 people quit on me, ever. One was “graduating” in a way. She was a senior designer who got a director level position and I didn’t have a director position for her. She had been with us 3 years and was totally ready for the role, so I was super happy for her (as much as I didn’t want her to go, I couldn’t compete with her offer and she contributed a lot over 3 years). The second left because he wanted to be closer to family on the East coast, again, something I can’t control. The third however quit to take what I perceived as a crappier job for a $4k bump working for the CEO’s daughters start up (no defunct), and quit as I was handing him a bonus check in front of the president of the company without giving me any warning. I had been personally mentoring this young designer as was totally caught off guard. Naturally I was not happy.

My point is, you only get to quit a job once, make sure you do it the right way and for the right reasons. It will have a big impact on your career later because your network and your reputation will be your most valuable asset.