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Does it matter what size (283, 305, 350, 400) SBC engine is swaped as far as ease or parts availability? Any advantage of one size over another?

The 350 is the most popular because it's the biggest displacement that's most readily available. Stroke a 350 to 383 seems to be the big deal right now. 400's are somewhat rare but if you can locate one, get it anyways. The 400 needs a specific harmonic balancer and flexplate but things like intakes, headers, covers and the like will interchange with other Gen I motors. 305 motors can be found anywhere but they lack power compared to the 350.
But basicly, any V-8 engine will be leaps and bounds better that the stock 4 cylinder motor. You can fit any smallblock in to your truck now, and later on you can build a killer motor and it will be a simple engine swap.

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Previous setup: 4.1 Buick V-6/TH 350
Current setup: 400 Small Block Chevy V-8/TH 350
9" ford rear end/short bed/blue
What do Water, Electricity and Humans have in common... They all travel the path of least resistance.

The problem with a 400 small block is the bores are married to each other. Coolant can't get in between them and it causes hot spots. It might be ok for a little LUV, but in a full size truck towing a boat, they were a BIG problem.

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OK, I'm over it. Where's the beer?

My Dad still drives his 78 4x4 with a 400 in it. 28 years and over 400k miles of towing farm equipment (sometimes extremely heavy) all over hasn't caused any problems with it. At least nothing that required pulling heads, the intake, or anything much worse than a timing chain. And to think, two teenage boys learned to drive (and 4wheel) in it too. I know there is always an exception though, and this is probably one of those.

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95 Isuzu Trooper Daily Driver
86 Isuzu Trooper reliable backup
77 LUV 2wd stock beltway blaster (resting)
79 4x4 LUV project: 2.6L, 5spd, 31s (eventually)

MEPR: Man, my 4x4 makes all other LUVs look good

The basic design of any siamezed cylinder engine isn't that much to have any concern over. It's true that it's not optimum but any motor can fall to overheating.
Buick 4.1 engines are siamezed also and they're rock-hard reliable. As someone who's built both V-6 and V-8 siamezed designs, having concerns about cooling and hot spots are a waste of time. The only real issue i can see with these motors is that once the motor reaches maximum over-bore, that's it for the block. Resleeving a 400 or a 4.1 Buick will not work. The material thickness will give way and crack when trying to press in the new cylinder liner.

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Previous setup: 4.1 Buick V-6/TH 350
Current setup: 400 Small Block Chevy V-8/TH 350
9" ford rear end/short bed/blue
What do Water, Electricity and Humans have in common... They all travel the path of least resistance.

Advantage is...Bigger is better. Disadvantage (minor) is the bigger you go on SBC displacements, the worse the rod to stroke ratio gets. set a 400 up right and you will never have cooling issues with a factory 400 block.

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1978 LUV Truck 2WD
450 "Small Block" Chevy
3.70 Ford 9
28x10 Goodyears

In reference to the farm truck being the exception to not overheating or needing anything except a timing chain, let me add my own. I had a 350 in my 87 half ton. Ran great got 22.9mpg highway. Didn't add anything over it's life span. Then one day at 315K miles it started loosing antifreeze out the tail pipe. Both heads were cracked. I was accused of overheating it. Nope, never happened. Anyway put in another crate motor. Figured the original was good why not repeat. Well it should have been called a 'crap' motor. 13mpg slowly creeping up to 15 then up to 16. Started using oil around 80K. What a piece of crap.

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Let me xray you, you will feel better.

Targetmaster motor... Hecho en Mexico.

I think your 22.9 mpg mileage was exceptional so when you started getting more normal mileage in your truck, it kinda felt like a letdown. My 89 chevy 350 TBI motor gets 15-17 at best with an overdrive trans. its never come close to 20mpg. its has about 230K miles and uses a little oil but it was my fault for loaning it to my bro for a couple of months who i know doesnt check that kind of stuff.

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1978 LUV Truck 2WD
450 "Small Block" Chevy
3.70 Ford 9
28x10 Goodyears