2-Where does a regulator go in my flow? Make/model recommendation?
As late in the system as you can get it.
One thing you need to remember is your system is only going to flow as much fuel as the smallest port in the system will allow. Use a Holley deadhead regulator and you might as well plumb your system with 1/4" line. You can run -16 line from the tank to the pump and from the pump to the motor, but if you end up stepping down to -6 or -8 line to feed the carbs, that -16 line has suddenly become reservoir and not massive supply. It will never flow more than the -6 or -8 line will allow.
I always recommend a bypass-style regulator and a fuel log, for high volume applications. Yeah, I hear everyone groaning about running a return line to the tank and a clunky-looking fuel log, but when you need consistent volume, this is the safest way to do it.
Plumb everything with minimum -8 line/hose/fittings. And stay as far away from 90° bends as you can. If you have to make a 90° turn, do it with the hose end and make sure it is a tube bend and not a forged-fitting bend. Lay your hands on some 1.750" aluminum tubing, a bit longer than the spread between your end-most carb fittings. Weld a couple of end caps to the tubing. Lay out some -8 adapter fittings along the run of the tubing as supply locations to the carb inlets. We're not looking for just a convenient way to get fuel to each carb inlet, we're also trying to get some additional volume as close to the carbs as we can. When you're finished, it isn't the prettiest piece you've ever seen, so have it anodized to "prettify" it.
Supply one end of your log with output from your fuel pump and attach your bypass regulator to the opposite end. Use a simple two port regulator and you can plumb a pressure gauge into the output port. As for recommendations, talk to
Aeromotive and see what they have to help you out. I don't know if they will have anything that might already be boost-referenced, but I'm betting they do. And remember, it only costs a bit more to go first-cabin.
Remember a very basic point most people overlook or fail to understand. A 2X4 carb application is a lot easier to make happy than a 1X4 application, because you have twice as many float bowls to serve as mini-reservoirs for the fuel.
I've seen drag cars leave the line so hard, that a Hi-Vol pump cranked to 20 PSI will drop to about 6 on leaving the line. The harder that car leaves the stoplight, that liquid is wanting to stay back there at that very same redlight.
Which is why the drag cars that can, all use front-mounted fuel cells. And that is also where the fallacy of ginormous fuel lines from a rear tank leading forward comes into play. We think (erroneously) if a -8 supply line is a good thing, then -10 is better and -12 is even better yet. But when you remember the fuel in that line has mass, a -12 supply line can actually be worse than a -8 supply line. Because the column of fuel in that -12 line has more mass and is going to be even harder to keep moving under hard acceleration. For something capable of 60 foot times any faster than 1.10, -10 is about as big as you want to get with a rear-mounted fuel cell. Anything larger crosses over into the diminishing return range.