First thing you need to do; Figure out what YOU want and make a list "thumbsup".
I can tell you from experience, if you write it down, plan for it and save for it, more than likely you will finish it. I can't tell you how many customers and friends I have dealt with that started in one direction only to change minds mid build and end up spending 2 - 3 times the cost. Make a list. Write it down, type it into the computer, put in on the refrigerator, or whatever, but make a plan and stick to it.
If this is something you will daily drive and see lite drag strip duty, think about efficiency and durability. The 350 will be more durable and efficient. Any motor built right will last. But the 350 has been around forever and is tried and true. The manual transmission will get you better gas mileage and will indeed be more fun to drive. But a manual trans with high clutch spring pressure will wear you out driving in traffic. On the other hand, automatic transmissions have made huge technological advances and are most consistent at the track and easier to drive. But 28 MPG out of a high performance small block is not possible with an automatic like it is with a 6 speed manual. Plus high stall converters create more heat and heat ruins automatic transmissions fast.
I had built my wife a 1964 Chevy Nova Station Wagon. I installed a stock GM crate 350 motor in with all bolt performance parts. I had a 200R4 trans built for it and I used Bowtie Overdrives TV Cable kit and cross member. The wagon had a 10 bolt 336 geared rear end in it. It had a Edelbrock 650 carb on it and on the freeway, if you just cruised at 70mph, it would get 25 MPG. It would also ran a high 13 second quarter mile (consistent low 14 sec mostly though). The wagon was fun to drive, totally streetable, and reliable.
My orange 1964 Chevy Nova is a different story. It's more a show car that was also built to see drag strip duty. The car runs low 12's in the quarter and can be driven to the track. But in all honesty, it's a pain to drive, uncomfortable, and not super reliable. It's a standard bore and stroke 350 but with 11:1 compression, Sportsman 2 heads (with port work), solid cam, etc, etc. It has a built TH350 trans with 3500 stall converter, Ford Nine Inch rear end with 355 gears and locker. It barely runs on 93 octane and prefers to be mixed with race gas. I honestly drive my nova less because $5 a gallon 93 octane is just not worth it, when the car gets maybe 9 miles a gallon. Not only that, but with so much horsepower, I just want to act a fool in the car and it's safer for me and my family if the car sits in the garage:lol:.
I share this with you so you don't waste money and make a poor decision. It is a true statement that there is no replacement for displacement, but technology has come along way and getting more horsepower and torque from smaller cubic inches is now possible and it is easier and cheaper to do so. You would be better off with a mild 350 that at least has decent chance at reasonable gas mileage and adding nitrous or a super charger instead. Unless you can honestly say that money is not an issue and neither is $5 - $6 a gallon Premium gas.