Vae Victus
Posting more than I know
Yea, you should junk that thing and put in a 2F. 
Sorry - couldn't resist.

Sorry - couldn't resist.
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You won't hear me arguing that! However, in defense of V8's - mine's an amalgamation of about 3 different eras of engine which could be part of the problem. 283 block/heads, aftermarket 350 manifold with a Buick carb that's about 2X too big for the engine...My truck has been aptly named.
I run an SBC400 with a Quad. I bought a reman carb from Jegs, then had a carb guru set it up for me. Runs like a scalded dog! Especially after installing an HEI distributor. Would I live to have a 40 with a 2F? Yes. I won't give up my SBC though. I love the power, sound, and availability of parts too much!
283s issue is they just have too small of a bore to put decent heads on them. The long stroke, small bore is such a torquey motor, though, that I bet it's pretty good. That said, I'd pull a Vortec out of a 97-99 Chevrolet truck/tahoe, rebuild it without a new cam (be in it maybe $300 including purchase price) and run it with efi. It's a best of all worlds - an LS doesn't bolt in place, but the last gen of the sbc really was the right engine. excellent torque, excellent dependability, good fuel economy, dirt cheap to build and parts can be purchased at your local 7-11 (okay, maybe the last is almost an exaggeration).
were I to stay Toyota (not my flavor, but it's an option)... I'd do something in a 2JZ motor but without any turbos.... or a diesel. on my build, it's still possible that I'll use the 6.5 diesel I have rather then the gas motor (the $300 tahoe motor)...
my tip for oil pans is use the old-style gaskets with just a dollop of silicone in each corner. I've used the one-piece retrofits and think they all suck... sorry for my language, but where I can easily get them not to leak with the cork and rubber gasket; I've yet to be successful with the one-piece. Worse is you have to buy longer studs/bolts...
that said, pulling a couple bolts on the front and one end of each shock would make that job a lot easier... to the point that the time it took to take it apart would be less than struggling with it (a lesson that I took a long time to learn).
I so rarely do a leak-down test. To me a leak down test is the way to tell me whether or not the head is leaking or the rings. When you pressurized the cylinder, did you hear air escape from the block or the intake on the >10% cylinders? I also don't do the test with the piston at TDC, I do it from BDC because cylinders, as they wear, tend to lose more metal at the bottom then at the top.
Do you still have the spark plugs? I'd be interested to see what you saw with them.
But as a general rule, I rebuild motors that have wildly dissimilar compression readings. That one doesn't hit it - it sounds to me like you may have leaking oil seals and/or a burned valve or two. The 283 was never a motor designed to run on unleaded fuel, so unless the heads have been rebuilt (and a very expensive rebuild it is), odds are it doesn't have bronze guides or hardened seats. That causes problems in a couple ways - 1) the lead protected the valve stem from wear - so without any kind of lubricant, the stem will wear; and 2) the lead cushioned the valve when it landed - especially on the hotter exhaust port. That means that it will overheat the valve which will cause it to warp slightly and become what we refer to as a burned valve - burned valves don't seal well, and the hotter they are the less they seal. Which brings us to the test at cold... it may not have told you much at all (other then the direction the air is leaking from).
If you are thinking about pumping any $ into the 283, check this out:
http://www.summitracing.com/parts/nal-10067353/overview/
And it comes with a 12 month warranty
a bit of oil isn't really anything to worry about on an older motor. Keep in mind, those motors have a crankcase vent system that vents to the road through a sizeable tube. My concern would start at built-up carbon, or smoke-screens.
why it costs so much to rebuild? volume, everyone does 350s (even me). As there is no substitute for cubic inches 350 > 283, that means the 350 gets the love and the 283 doesn't. That said I've spent crate-LS7 money building (not yet done, mind you) a twin turbo 455 Buick - but it's for a special car and special project.... which is kind of entertaining to me because many times the smaller motor is a better option for whatever is being built.
a bit of oil isn't really anything to worry about on an older motor. Keep in mind, those motors have a crankcase vent system that vents to the road through a sizeable tube. My concern would start at built-up carbon, or smoke-screens.
I'd run it until it died or became so smokey that the cops stop you and give you pollution tickets.
To "fix" the oil leak issue, I'd use a hotter plug so you don't have to change it as often (has a tip that reaches further into the cylinder and won't foul as quickly)
As for accessories - you can bolt everything but the harmonic balancer from your 283 to a 350. I presume, of course, that the 350 is of the two-piece design - otherwise you'll have to get a new flywheel as well. That said, both of those parts are less than $50.00 new.... stock flywheels are $30.00 and stock balancers for a 350 is $16 (and for those prices, I'd never reuse either).