I am looking for a highly directional antenna to set up a point to point with my brother in law that's around 35-40 miles away, and also a good antenna for him to try and hit repeaters in a nearby city.

I am also probably going to try and use it to hit the ISS.

Would something like this work?

http://www.amazon.com/Able-Signal-Amplified-Motorized-competition/dp/B00M5RXL5M/ref=sr_1_28?ie=UTF8&qid=1414110991&sr=8-28&keywords=HD+TV+antenna

ETA: I know I could receive on it without any issue, I would just be worried transmitting through it.

Cheap? Hard to beat the 11 element yagi I was given...
Search Quagi and homebrew you a couple!!
I'd pass on the TV antenna linked. Ymmv

Search "2 Meter Yagi plans". I made a 5-element Yagi from a couple of defunct TV antennas.

A friend (S9SS) at the VOA Sao Tome site made a Yagi using strands unwound from a scrap piece of guy cable and used it to work the ISS. The elements were kind of corkscrewed, but it worked. Picture HERE. Note part of one of the VOA arrays in the background.

They are plenty of yagi plans available online.  Some easy, some complicated.  The simple ones will usually be ok.

Keep in mind at that distance height of the antennas will be as important as the antenna gain.

No.  That antenna won't work.  You will fry the preamp the first time you hit the transmit button and fry your transmitter soon after.

You can buy or build a yagi for 2 meters for less than the price of that TV antenna that will work much better for you.

Homebrew Quagi was the first thing that popped into my mind when I saw this too!  Forget the TV antenna.  There are commercial Ham antennas if you need to purchase instead of build, like this and many others.
http://www.dxengineering.com/parts/hgn-vb-214fm?seid=dxese1&gclid=CLeku6GVxMECFUKCMgodknwAGA

Whats the advantage of a quagi over a yagi?

It's supposed to combine all the benefits of a Quad and a Yagi.  I've never tried to build one because commercial 2 Meter antennas are inexpensive due to their relative small size.  Years ago they were all the rage and you can build them out of next to nothing if you need to.

http://members.optusnet.com.au/jamieb/quagi.html

I love the cost/gain ratio of a Quagi, and have always wanted to build one. Thing is, all the photos show them as horizontally polarized: does it change the measurements to build them the the directors vertically polarized? Does that actually make it vertically polarized?

The ISS is reachable by a HT and a tape measure antenna. Don't forget extending contact by using Doppler frequency shift involved when communicating with orbiting objects.  Talking with the ISS lately is more reserved for children related programs and planned out weeks to months ahead of time using split frequencies generally not published ahead of the planned contact time. There is a APRS packet that is active on board the ISS.  

Link

Trying to make a 35 to 40 mile on 2 meter will depend on terrain even with a high gain antenna.  Orbiting objects have no terrain to block contact overhead but are limited by their orbiting path.

You see them horizontal because most guys build them for weak signal SSB & CW work.  If the elements are flat it's horizontally polarized, flip it 90 degrees and it's vertically polarized.  I know with normal quads you feed the driven element at different positions for different polarization, but I believe you would just build the Quagi as shown and rotate the whole thing 90 degrees for vertical polarization. Thoughts?

Directional antennas may not be the only answer.  You'll need to elevate both antennas.  It all highly depends on terrain between you and the person you are trying to communicate with

Look at www.hamuniverse.com, click Antenna Design on the left side, and keep scrolling down.  Lots of
plans for 2m antennas.

Reminds me of two yagi's I modified once. I took two commercially available 8 element yagi's (UHF) that I had laying around, some RG-59 and a stick…built a co-phased array (much like Cushcrafts only cheaper). Co-Phasing can sometimes help…isn't always practical though.

Many moons ago I built a 3 element copper loop "quad" (the elements were actually round) out of refrigeration tubing, fiberglas rods, and PVC pipe.   The antenna worked great and it was super easy to build.   So it was a great experiment, but really it didn't have long term usefulness, being somewhat heavy and flimsy both at the same time.

The commercial built yagis from Cushcraft or whomever are really hard to beat, because they have mass produced custom hardware to hold the pieces together which would be difficult and expensive to produce in a home made project.   For me, the cheap and easy yagi & quad projects I have seen online leave something to be desired.

Not saying a fellow with ingenuity and a basic set of machine tools couldn't build something as good or better than the commercial products, but he wouldn't likely save any money, when you can buy a 4 + 7 dual band yagi (for example) for less than a hundred bucks.

^ This.  A few years back I had 31-mile QSO from the top of Stone Mountain, Georgia, with handhelds putting out one watt.  If you have line of sight, whip antennas and low power will work fine.

http://www.ar15.com/archive/topic.html?b=10&f=22&t=636439