Longbox is right, you can eliminate the oil=line to the head on your 1961 235. When there wasn't detergent oils, the oiling passages got gummed up and the fix was that bypass line to ensure oil to the head. With modern oil and a good rebuild you should be fine.
The amount of bore you'll get will be determined by the machineshop when they check over your block. If you've only got one or two cylinder really bad you can sleeve those and bore/hone so they all match rather than boring them all 60+. I'm not sure the max overbore and think it varies from block to block since the castings in 61 werent as precision as they are now so there might not be uniformity in the width of the cylinder walls. I have heard of people way overboring and using v-8 pistons, but that may be on the 261 only.
There is a lot of debate on dual carbs or a clifford's manifold with a progressive 4 bl. The theories are that with the carb in the middle the outside cylinders don't get gas so use two carbs. The other theory is that clifford's design evens out the flow and 1 4bbl is easier to tune and maintain than 2 1-bls or 2 small progressive 2-bls like the holley-webber or carter-webbers Langdon sells.
There is also a debate on how to heat the intake best. The stock one was heated with exhuast gas. Some people thing water is better.
Then there's the header vs. cast dual vs. split manifold debate.
In the end, its probably personal preference and intended use as much as anything. I went with fenton's, offy dual manifold heated with water and an HEI igntion. I also went with solid lifters 'cause I've heard these engines have a tendency to have the #3 & #5 hydraulic lifters collapse and just didn't want to deal with it.
If you havn't gotten the block to the machine shop yet, you should consider modifying it for full flow oil filtration. Here's a link with instructions.
http://www.speedprint.com/Deves50/oilfilterinstall.php HEI is a worthwhile mod.
Drilling and tapping the front bearing cap to install the lower timing cover bolts from the outside is worth it.
Hardened valve seats is probably worth doing.
Balancing the pistons, rods, crank, flywheel and clutch cover might be worth an extra $150.