Solution 1:

Yes. This article answers most of your questions.

Is there special outdoor-rated cat5e/cat6 I should use?

"Preferably, special exterior or direct burial CAT5 cables should be used for outdoor runs instead of ordinary CAT5."

If put it in a dug trench, do I need to put it in conduit?

"Exterior-grade Ethernet cables are waterproof and thus do not require conduit."

If I run parallel to electric, how much separation do I need, and do I go UTP or STP?

"5-20cm (6-8 inches) and at least that far away from power lines or other sources of electrical interference."

If I do an overhead run, how should I properly ground it against lightning?

"Accordingly, CAT5 surge protectors should be installed as part of outdoor Ethernet networks to guard against lightning strikes."

Solution 2:

I did the same with conduit. This way you can run regular wire inside and if you ever need to run additional wires you just feed another one through. I did this for my securtiy system and added the Cat 5 later, I am not sure that I wouldn't have just used wireless had I not already put the conduit in there.

You can now purchase outdoor rated cable, that is designed specifically to resist sunlight, moisture, and most other things.

Edit: Just a minor detail, at least minor until you need it. When you run the conduit be sure to pull a string through and tie it off at both ends. You will use that to pull any additional wires through if you need to later. Thanks to Chris Noe for pointing out my omission.

Solution 3:

I'd use conduit for ease of maintenance. If a cable goes bad, you can pull new cable though the conduit with out having to dig up and rebury the cable. I would still use an exterior rated cable.

Solution 4:

Won't write up a full article as others seem to have done a lot better than I could... however...

No matter the temptation to save money and use standard cable - DON'T!

A few years ago, I had to go to a school that had used standard cat5 cable all over the place and across flat roofs to go building to building.

They called me in after a lightning strike killed EVERY rj45 port on switches, routers, servers, desktops... and even fried IP cameras and print servers - Everything you can imagine!

Changing over 300 NIC's was a very long job and it was expensive to replace the other network equipment.

They are now using fibre optic... Not that much of a practical solution for home networking if you already have equipment, but certainly go proper - conduit, trench e.t.c.

(or if you do go cheap, remember my contact details for the future in case you have a big job coming!!)