I've jailbroken my AppleTV2 in the past, but found it to be more hassle than it's worth. When new features launched in the past I've had to go without until the jailbreak community comes up with their own version of the features, or a way to jailbreak the newer update.
Also, with Airplay mirroring on newer macs (and apps like AirParrot for older systems), i can stream any video I want to my TV anyway. So really I don't understand what all the fuss is about jailbreaking?
Jailbreaking has become about as easy as it's every been. Nowadays you don't even have to use the command line.
1. Jailbreak with SeasonPass (completely GUI-based)
2. Use the free "Nito Installer" application on your mac to install Nito, XBMC, and Bluecop's plugins (for Hulu, Amazon Instant Streaming, Free Cable, ESPN3). Installing these takes one click. Literally.
Check here for updated instructions:
https://forums.macrumors.com/threads/1305573/
As far as waiting for the next jailbreak: yes that is a tradeoff. But I've had jailbroken Apple TV2's for about two years now, and generally the "new feature" that Apple adds is never so revolutionary that I mind waiting a few months for the jailbreak to be updated.
So, for me the only "hassle" is updating / re-jailbreaking roughly once a year. But it generally takes less than one hour to jailbreak and deal with any bugs or unexpected issues, and less than 20 minutes once you've got the procedure down.
If you don't see the big fuss about jail breaking, then I'd advize you to sell your Apple TV 2 on ebay. Unjailbroken, you can probably get at least $200 for it. If you jailbreak it and install some XBMC plugins (via the procedure I linked above), you can probably get $300 for it. Use the proceeds to buy a refurbished Apple TV 3 (for $85 plus shipping) from Apple.com, and pocket the remaining $215.