Extending single network between 10 buildings with multiple Trendnet TEW455APBO AP's

We are looking at extending an IP camera network over 10 buildings each about 500 feet apart. The buildings are situated perfectly side by side and the same dimensions so there is no line of site except between each pair of buildings. Originally my thought was put one Trendnet TEW-455APBO AP on top of the first building that has the with the router and internet connection and then put 9 more of those AP on top the remaining buildings and aim them all at the first AP. I found out that we for whatever reason cannot put anything above roof height. Don't ask me why. So we are forced to mount them to the side of the building but then only the other building next to it would have line of site to it.

So my other thought was to put 2 of these AP's on each of the remaining 9 buildings, one on each side of the building. The first building would still only need one AP since its first link in the chain. So in essence each of the 9 buildings would have an AP mounted on each side of the building, one to receive the signal from the building before it and one to retransmit the signal to the building after it. Will this layout work? I would have thought all the remaining 9 AP's would need to be looking at the first AP rather then each other in order to function but I could be wrong.

Thanks in advance,
Adam

each successive AP will wrap the data it receives in a layer of information, then strip this off when it gets delivered. the throughput through each successive hop will get lower and slower. by the 10th hop the network will be about the speed of a 300 mps dial up modem from the 80s.

Yeah this will suffer quite a bit from 1 side to the other. 10 hops and 300 feet between is really going to kill your signal unless its got really accurate signal regeneration or projection. Also, your perception of how APs connect to each other is wrong. AP 2-10 won't all project their signal to AP 1, they will relay it to the next strongest link in the chain. So AP 10 would go to 9, 9 to 8, 8 to 7, all the way back to 1.

However, there are external antennae that can be bought that can be used for accurate long distance direct line of sight communications.

Check out something like the TP Link TL-ANT2424B antenna and you'll see what I mean. Most antennae can be swapped with upgrades since they use standardized connectors. If you can get one connected and pointed correctly, you could probably have some fun with it.