I am going to install Debian on an eeepc this weekend.
The Stretch release being so close I am wondering if I should install that (and make sure the sources.list is pointing to the codename, not testing).

If there is any breakage that can be fixed through an SSH session I could handle it, but more severe breakage (especially broken networking that prevents remote support) would be a problem because the machine is 450 km away...

Given the above scenario, does it sound reasonable to go with Stretch in its current state or should I stick with Jessie? (I haven't gotten my hands on a stretch install yet...)

That is why they have ILO.

Unless you configure the loader to automatically reboot to the old install, then
look at logs, it would be risky.

Even if you had a test system at hand and did a few weeks tests it doesn't mean that the far away system will be stable.

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Thanks for the input jefro!
Phew, that I'd like to avoid.

I guess I understand that it is a bit risky, (that's why I was asking for opinions), the question is whether the risk is reasonable. Note this is not a mission critical netbook, the owner has a second laptop and both are used for private purposes. So if the netbook was unusable for some weeks until I physically get my hands on it to fix it this wouldn't be the end of the world.

My gut feel however was that such severe breakage would be pretty unlikely at this point, on the other hand I also read that testing does not get security updates "in a timely manner", whatever that means.

Still somewhat undecided... Opinions from people running stretch currently welcome :-)

I used Debian Sid for a five years and did not experience any issues (eventually that computer went to the great recycle bin in the sky). I'm now running it again.

Sid is more stable than many releases.

Sid is experimental. I suppose it depends on one's definition of a "problem". I sometimes mix sid and testing on the same machine. Problems are only problems if you can't solve them.

Arf. Just figured out that there are no live images for testing. Which is obvious if you think about it.
That changes the equation. I'll want a fully preconfigured cinnamon desktop because my time to set this up is limited.

So this will mean I'll go with jessie. Sorry for the noise.

Incorrect! Sid is unstable - experimental is experimental https://wiki.debian.org/DebianExperimental