Hi Korie,
Sorry for the delay in answering your great questions. I have been unable to write due to some eye problems. They are finally starting to clear up...so here goes.
First of all, you are taking the best step forward right now by starting to look into freelance writing before you actually need to depend on it.
I am glad you asked this detailed question as I have been wanting to do an extensive series on freelance writing and your post has given me the push to begin my research.
Years ago, I was a freelance writer and did very well after I found the area I liked that also paid me what I needed to make. Honestly, finding that combination took me a little while. In the end though, it was worth it.
I will answer your specific questions as best I can right now. However, I will keep them in mind as I begin to research this area to find out what is happening today. My experiences years ago cannot speak to what is available or even possible today.
Question 1.
Is it possible to make 2K/month freelancing, or would I need to supplement with part-time teaching gigs (i.e., picking up a class at an adult school or junior college)?
In general terms I would say yes it is possible to earn 2K/month freelance writing. However, there are a lot of variables you will have to look at before you know if you, in the area of your interest, will be able to make 2k/month.
First, do you mean 2k/month gross income? Or do you mean after taxes (two very different numbers).
Second, what type of freelance writing do you think you would be happiest doing right now? The actual type of freelance writing will dictate income numbers.
Question 2.
At that time, I'll have two years' worth of clips from my BOL sites, which are in the Travel and Health channels. If I want to write for publications in other areas, do I need clips in those areas specifically or will my current BOL areas be enough?
It all depends on the type of freelance writing you are looking to do. If you want to work for specific publications then they will want to see clips that are written in a style that is similar to theirs, but not, necessarily on the same topic. If you want to write for companies in these areas you can use your BOL clips and do some samples for them when you interview.
Question 3.
Is there anything else I should start doing now to make this a seamless transition?
I would suggest that you first define what type of freelance writing you want to do. You can research online in a topic area like Health or Travel and see what types of articles are being bought, as well as what kind of blogging jobs are available.
Figure out what kind of hours you want to work in total, and then narrow down the topic area you would really like to specialize in.
I hope these quick answers are a little bit of help.
I have begun some detailed research and will do a series of freelancing articles in the coming weeks. I will keep your questions to see if I can find more accurate answers after my interviews and research.
This sounds like a lot of fun!!
Enjoy your day,