If I'm reading this correctly, I believe you want to build one antenna to service 8 units. As far as signal goes, my guess is that once you run the splitters (3 all together, a double, each side going to a four off) you're worried about loss of signal to each unit, especially if they are running more than one television.
That being said, I'm thinking that a signal booster at the entry point to each unit (before they split to any televisions) is going to be your best bet. I don't know what your local cable service is like, but if they run an analog system like Time Warner still does in the northeast, you can probably locate more than one signal booster, complete with power inserter (connected by coax) to suit your needs and for little to no cash.
This *should* resolve the post splitting signal loss and alleviate the concerns of where to plug in a booster pre splitting (which, if you can, can't hurt either).
The other option, and I'm still investigating the do-ability of this, is to locate a 4-4 switch from Dish Network (again, complete with power insterter that goes inline with out port #1) and use 4 double splitters (should be less than 5dB loss on any given line, but power should boost the signal) to reach 8 units.
Just a couple ideas, but feel free to share what you do and how it works.