Look for more tax breaks. As a self-employed person, you should have access to a lot of tax breaks. Maybe you are not accessing them all.
I do question having that $600 student loan if you have enough money to pay it off (using your emergency account). Maybe you should pay it off more aggressively? The only reason to not pay it off would be if you had another loan which had a higher interest rate. If it’s your only loan, maybe you could just pay it off and keep the extra.
Certainly looking at your situation, you are playing it safe, but if you want to get ahead, you will have to take some risks. There are trade-offs and you will have to ask yourself if you are willing to do that to get ahead.
You’re right in that it is a different playing field for you than it was for your parents. It is not easy to just get by nowadays. You will have to work smarter (and I do not mean just your job, I mean in every aspect of your life). Superior financial skills, appropriate risk-taking, and keen analyses are required of every person who wants to get ahead.
(I recommend viewing the Robert Kiyosaki PBS Special that they run every time they hold fundraising and the book The Inside Guide to Real Estate Investing Loopholes by Diane Kennedy and Dolf De Roos).