Hi Ryan,
I found myself in a similar situation and took the leap into part time real estate almost 2 years ago. Real estate definitely comes with its fair share of fees. The first year is going to be the most expensive year as it comes with all the upfront expenses classes, license exam, license, MLS... etc. You can get an excellent break down of all the expenses for Colorado specifically here and what the basics of the class entails.
I did not do a single deal my first year so was out the ~$2k. Since then I have found some great ways of prospecting and finding deals. I have been able to close two deals this year and I am now ~$5k profitable since starting out. I am thinking of transitioning to full time as the prospecting piece is a challenge with a full time job.
It really helps to save on fees by working with a discount broker.You keep way more of your commission and it really helps to make it profitable as a side business. The bigger brokers will claim to give you leads and excellent training but in reality they will give you little hands on experience and and no leads. You will burn cash at an alarming rate.
I live in the Denver area if you ever want to connect. Next deal I get I would be happy to show you how it all comes together and what it entails.