Will the signal reach?

Yes, you'll need a relatively high-gain antenna. But first, you need to rent a chainsaw and a bulldozer to get LoS.

It might be cheaper to just share files by attaching them to email. Or sending CDs via snailmail.

You're going to have to get the antennas up in the air...period.

Mounting both antennas on your roof peaks isn't going to work as teh houses in between will block the signal. Without doing a Fresnel clearance plot, I'm going to guess a 35-40 foot mast at one end and a

The signal will not get there at all. If you were somewhat close to each other (ie. a couple of doors down) you could perhaps get away with some massive omni antennas.

Sure, the signal strength wouldn't be great, but you might be able to move a file the size of a movie to him overnight.

In this case I count at least five houses blocking your way.

You'll need to elevate it. Check all areas of your house thoroughly; if you can't find any area at all (be it on the side of the building, on a drainpipe, whatever) that has line of sight of his house, you won't be able to do it without mounting something on the roof.

It might not be too expensive if you can both get LOS of each other's TV antennas. Then you could mount the wireless antennas onto the TV mast - then run the cabling through the roof.

No, you don't have LOS to use either of those. They work best with LOS.

Both of those would work very nicely if you have LOS and Fresnel clearance.

Just by looking at that I can tell you you haven't a chance without LOS/fresnel.

When you factor in the expense of an antenna (be it a commerical one or a homemade), an AP/computer to keep the connection up, as well as all the cabling and mounting gear, it doesn't really seem worth it if you're looking to keep things cheap.

Then again, if you spend at least $150AUD (at each end) and have LOS and Fresnels at a particular area/elevation, then you could (keyword) get a nice connection set up.