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>Fire Ax
I'm not going to be melee-combating zeds if I can help it, so I'm going with this for its utility value. Not very useful, however, unless you apply magical properties such as "never gets dull/corroded and is unbreakable", though. All items in the top row can be found lying anywhere, so it's silly.
>Glock 9mm
Just a simple gun, more for defense against other humans than zeds. Why the heck would I want something with hard-to-find ammo and huge recoil just so I can feel like goddamn Clint Eastwood? However, its utility is also negligible unless also magical (ie: never runs out of ammo); I'll pick up other firearms somewhere else.
> ATV
A nice middle-ground of size and complexity. The humvee is too large/complicated to be useful, and the dirtbike too small to carry much cargo and/or passengers easily. I can easily find parts for and maintain/repair the ATV myself, something I can't do with the hummer. Segway is retarded: there will be nowhere to charge the thing two days after civilization collapses, and it's too delicate to survive in the dust out there.
> Gas Tank
The other items tempted me, but the truth is that mining and refining petroleum is something that can only really happen with large industry, at least cheaply. Gasoline would be THE MOST IMPORTANT resource (by way of scarcity) after civilization collapses, at least unless you intend to run from the zeds. Everything else I can survive without, but with no gas, I go nowhere. Also, due to its value, it would be the most useful thing to trade.
>Cortana
I don't have any reason not to pick Gay Barry (he's not really my type, but I'm not straight so the sex wouldn't be problematic) except that I fully intend to solo this little adventure. I don't want any dead-weight partners for anything other than short stretches of time when necessary. Also, an unkillable zombie-distracting-device would be quite useful.
>Zombietown
I would camp in place for a short time in order to build up my resources by having my magic gas can produce what is essentially liquid gold, and trading it for what else I need. I feel weapons and technology and communication equipment are not very useful for me, but medical supplies are. Also, I'd rather not be stuck in an isolated trap (survival vault) if security is breached and zeds get in. A place out in the country offers ample chance to just break down a gate and escape into the forest.
Basically, I'd be Kevin Costner from Waterworld, wandering between these places trading an extremely-rare resource (gasoline, rather than dirt) that is nearly impossible for others to get, but easy for me. I'd always have to be traveling, because if word spreads about me, someone might find out about the magic gas can and attempt to kill me for it. Staying in one place too long or getting close to others would result in death.