Well, disclaimer first - none of us, as I am aware are financial advisors, just an informal club.
But I think you are splitting hairs at $2000.
Let' say your stock is worth $1800.
If it was up 30%, that' um. . .(bad at math). . .well, you started with around $1400 and made about $400.
Capital gains tax is going to be about $70 depending on your tax bracket, not a hell of a lot of money but most people drop that on drinks on a weekend. Yeah, it sucks but now you pay it and put it into your Roth, where it will grow tax free and exit tax-free.
It's either that or just put $2000.00 into your account and just hold onto the investment. If you think the stock will stay put where it's at , try to wait a year - the tax is only 15% ( a relative bargain in the tax world - see what inheritance tax is over 3 million) - I think, check with an accountant. If you cash out under a year, it's taxed at the same rate you pay income tax on (kinda sorta double taxed).
Tax shielding is all about declaring that money "earmarked" for a goal (retirement, college).
Welcome to business/investing - you need to treat the IRS as a business partner.
Uncle Sam and I are in business together - he gets the oil for me to use by invading countries and I operate the business and assume risk.
Hint for the future - for Roth IRA's, I think it's better to start with mutual funds vs. stocks or ETF's - the trading fees will kill you. And sure, you can hold stocks long term but really, how long can you really hold something? You can't - companies come and go. You can usually buy mutual funds for free. Stocks will charge a trading fee each time, thereby eating your return.
So, if you are buying on a monthly basis, an ETF or stock can really eat your return. Instead of getting in at $100/month, you are only getting in at $93.00.
I simply use mutual funds as an "entry point" into my portfolio and then 1x/year "rebalance" with ETF's. I just bought a silver ETF so it will cost me $7.00 for the whole year. At the end of the year, if my Overseas Fund or Blue Chip fund has done well, I'll buy some more silver.
If silver has done well, I sell it off and transfer some assets back into the weaker performer.
If they both tank, well then I'm doing this:
If they all do great, I'll do this:
MORAL OF STORY:
1. Don't move things around often.
2. Pay attention to trading fees.
3. Take advantage of tax shielding as much as you can when appropriate.