https://www.facebook.com/groups/1138882606178838/ <--Join this group before deciding if FiTech is right for you, it was started when FiTech's were failing everywhere and customer support was non-existent. I'm not saying they're terrible (FiTech), but these systems are a far stretch from bolt-on-and-go.
I don't know. Modern -factory engineered OEM- EFI is fantastic, when its MPFI or Direct Injection. TBI isn't that beneficial over a carburetor, the main issue (which is magnified with forced-induction) is improper fuel-distribution which isn't solved with TBI. Yes you can data-log, and spend countless hours looking over graphs and tuning. I would like to say these systems would prefer a modern style EFI camshaft with 114-116 LSA (low-overlap & minimal reversion) in order to self-learn easier. Some guys get them to run with large(r) than average camshafts, others don't. For a 440, I would choose something mild, like the .528 MP solid with 112 LSA.
Most problems with carbs (poor starting, fuel-boiling, etc.) are associated with mechanical fuel pumps and no return system; which both will be required with an aftermarket TBI unit (can't forget a good regulator). Please don't be a victim of the command center that FiTech offers, complete JUNK that has failed nearly everyone (i've been on the group since the beginning of FiTech as I was initially interested), so yes, you'll need a true return style system despite what they may tell you! My engine with a 259/267 @ .050 SFT camshaft will start up and idle immediately out of the car, absolutely no drama, with an 850 double-pumper. Yes, you'll need a Wideband 02 gauge in the car to tune a carburetor properly, but really, shouldn't any performance engine have one in 2017? About the only application I would go TBI would be for an older off-road rig, but then again, Holley has specialty carburetors for those applications as well.
I just have this -awful- feeling that a FiTech would leave me stranded on the power tour or cruising the coast, it's another 'lets pray it doesn't fail item' as there are no local parts available to fix it on the side of the highway. If the quality-control was better, maybe I wouldn't worry so much, but from what I've seen on that group; they are no different to me than 440source at this point. Lots of issues with Holley Snipers etc. as well, so I'm not saying FiTech is the only one and that many issues aren't derived from improper installation.