I'm getting a bad case of analysis paralysis. I'll explain my thoughts and I need to know where I'm going from logical to stupid.

I have symptoms of an oil pump o-ring on the way out. The obvious idea is to just replace that part. The problem is it makes sense to swap the timing set too since I'm already there and I have 200k on my stock setup. I could stop there and make it easier on myself, but since I'm already there it'd be the perfect time to swap the cam instead of tearing into the motor again later. Along with the cam I should probably do fresh lifters thanks to the high miles, but that means pulling heads. If I pull the heads it'd be stupid to slap the old heads back on since they're going to be the weak point in the build so I may as well go with some ported 243s while I'm there. So the worn o-ring is all of a sudden a couple thousand and a week of smashing my knuckles. Now I'm not even interested in starting the project because of how big it'll be lol
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How much do you wanna spend here? Like mentioned above you might be better off with a totally different setup

 

Drive it til it fails and understand its best racing days are well behind it or trust your gut and freshen the build. You dont have to get crazy with cost if your careful especially if your willing to go iron block. If it were me and the car still runs and drives well? Start putting together another engine while your driving this one. Create a budget and stick to it. A couple grand can get you lots of fun if you do the work yourself and research good combos. If you go 6.0L I'd suggest 243/799 heads or step to the square ports.

If you simply want the cheapest reliable and are willing for some down time? Fresh valve job on your stock heads, new lifters trays, LS2 timing chain, 216/220 cam, GM blue springs, fresh gaskets likely needed, check trunion bearings, reassemble tune and go ( watch for inj duty cycle ). Cost less than a grand and you'll be freshy fun again. Bottom ends are not typically an issue

 

do a compression leak down test to verify rings/cylinder walls are sealing. If the gauge shows leakage you can discern where the leak is ie. valves or rings. If all is well with the block side I wouldn't be concerned about a high mileage bottom end. Cam it ,oil pump , timing set , thinner head gaskets a tune and let 'er rip! 243 heads if you want

 

200k is nothing, I have 200k and everything but the motor has broken. I mildly built the motor anyways and there was no sludge, cam bearings barely worn, bores looked brand new, no deep scratches or anything, rings were still good, I didn't touch the bottom end. The LS1 intake was disgusting but I swapped it with an ls6. Between the intake ports on the head, there was quite a bit of buildup of oil and dirt. Threw on some ls2 heads anyways. Throttle body was filthy as well. Not a leak to be found. I'm going to keep running mine, it's also my DD. Replace any gasket you come across no matter what. I use felpro and never have a problem. After seeing what that LS1 intake looked like I got a catch can immediately from ws6store. I also recommend some msd wires, tr55 plugs and run good filters like wix. I always use Valvoline high mileage full syn and I've personally seen that stuff work so I will never use anything else.

I do have thoughts of building a 5.3 on the side though.

 

I've ran the **** out of plenty of high mileage engines, boosted nitrous etc. The parts don't get weaker with mileage. If it's got good compression, leakdown, and oil pressure go for it.

 

As of now the only issue is an oil pressure drop and flutter after extended drives. The symptoms seem to exactly match people who had their o-ring wear out. I also think the valves seals are on the way out since I get the slight puff of blue smoke if it sits for a week. Other than those the engine feels strong and revs easily. Idles at 600 rpm and only takes 900 rpm to cruise at 35 mph. It does have that sbc random stutter at idle, but I've never had a chevy engine that didn't do that lol.

 

Slap a new oil sender in it and see how it does. I had a bad sending unit do that before.

If you can get it to hold good oil pressure and it runs good I wouldn't hesitate to throw go fast stuff at it. But for now I think I would drop the oil pan, do the o ring and see how the oil pressure does. If it isn't better do the sending unit. If still not better you know what you gotta do. If it's fine then get all your go fast stuff together and set aside a weekend to do it.