Is there a recommended approach to entering Hebrew text? I see lots of it, and some questions/answers will require it (as transliterating into English works poorly).
I may be mis-understanding this question, but as far as I can tell it is about typing Hebrew characters for use on the site. If so, the best method which exists (if you don't have native Hebrew support and keyboard stickers) is Mikledet and amazing online Hebrew keyboard emulator which allows you to type with your keyboard and see the Hebrew on-screen.
Additionally, I would recommend pasting Hebrew text which is copied from elsewhere (eg. Bar Ilan, Mechon Mamre) into Google Docs first to format and then moving it over to this site. This is simply because Google Docs has very good RTL support and encoding so it clears most of the formatting issues you mayb have with RTL text. (For instructions on using RTL in Google Docs see here: https://docs.google.com/support/bin/answer.py?hl=en&answer=65166)
Modern versions of MS Windows, Mac OS X, Ubuntu, and, I'm guessing, other (at least modern) OSes have a "character map" program that will allow you to select Hebrew letters (and vowels) one at a time and copy the lot. Windows also has an on-screen keyboard and you can add a Hebrew keyboard layout; I'm guessing other OSes have the same.
Some instructions can be found here.
Adding ‎ (for the left-to-right mark) (and sometimes ‏ (for the right-to-left mark)) as necessary helps.
My personal policy is just to transliterate to the best of my ability and italicize. It makes it readable to the most people, which is the point of posting in the first place, and usually doesn't detract from the meaning. When transliteration loses some of the intended meaning (such as in questions about Hebrew letters or the like) I put in the original Hebrew.
A Hebrew keyboard is now built into Mi Yodeya, based on a script originally written by @HodofHod.
In the editor, click on the circled button:
to get this keyboard:
Clicking on keys on the Hebrew keyboard produces Hebrew. Typing on your keyboard continues to produce English. Mix and match as needed.
Use the ‏ key after punctuation that appears at the end of a Hebrew phrase to make the punctuation appear at the end of the word.
On my Android device, I enable a Hebrew keyboard and switch to it whenever I need to enter Hebrew characters.
Open Settings and tap on Language & Input. Tap on the settings icon next to Google Keyboard. Tap Input Languages at the top. Deselect "Use System Language" and then select any keyboard languages you wish to use.
If your native language is English and you want to type in Hebrew or Yiddish, you should go to https://www.google.com/inputtools/try/ instead.
How about using google tranlitrate? This link is only useful for native Hebrew speakers. At the bottom of the page there is a bookmarklet you can add to your links and clicking on it will tranlitrate what you type in the page you are viewing.