There should be oil all over the place. Everything should have a glossy film of oil on it. There should be oil in that recessed square-headed plug. The spark plug tubes should be oily.

Instead, everything's bone-dry. There's no oil getting to the top end – maybe a clogged passage, maybe the rearmost cam bearing out of position, maybe the rocker shaft installed wrong way round and/or clogged with baked sludge – and whichever valve guides were marginal-to-wonky before ate the replacements for the same valves.

Head's coming off again, for a complete valve job this time. New valves as required, hard exhaust seat inserts, all twelve guides, all twelve valve seats properly ground and lapped, appropriate valve stem seals, springs checked and replaced as necessary, rocker assembly disassembled, thoroughly cleaned and reassembled. All twelve pushrods checked for straightness and replaced as necessary.

Be aware that putting a nice, fresh head atop a tired/worn/high miles engine will often finish off the rings and/or bearings; you can wind up with an oil burner de luxe.
Nope.

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一期一会
Too many people who were born on third base actually believe they've hit a triple.

Some passage is blocked from the block to the head/rocker shaft, probably. Dan has got the possibilities there. I assume you have an oil pressure gauge and the oil pump is making pressure and the main/rod bearings are getting oil?

Lou

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Home of Slant6-powered fun machines since 1988

Could he just pull the rearmost rocker arm bolt out and spin the engine over and see if oil is coming up from the cam? It could have spun the rear cam bearing and be blocking the oil passage coming up through.

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2 Mopars come with Spark plug tubes. One is a world class, racing machine. The other is a 426 CI. boat anchor!

12.70 @ 104.6

As it appears based on the previous vids, that it's already burning oil (even in the 3 running cylinders). And this isn't a new issue.
It must be bad/stuck rings, eh? Engine has around 75k miles on it; if that means much in conjunction with its sitting time.
I'll have to do another compression/leakdown test to confirm (& adding oil to see if compression improves). I don't remember the last numbers.
Do you think it's worth the head repairs considering the wear/age of the block? Also consider, the oil burning + lack of flow. If it takes any work to the block, I certainly do not have the tools or equipment/shop to arrange that, unfortunately.

Here's a theory:
Oil getting past rings; engine burns it; leaves behind nasty buildup; buildup gets stuck behind intake valves and accumulates (here's where I'm skeptical - wouldn't the exhaust valves be most affected?); because of tight guides, the valves get stuck from buildup + when warm, they thermally seize up from metal expansion (indicated by the fact that I could press them a bit after some time, albeit sticky).

This theory kills two birds with one stone. It's either that, or the oil burning and sticky valves are two separate issues.
But the third chirper is still: why is there no oil on top-end...
I don't understand why that'd happen again after flow was restored following the "valve job". I remember now that he did send a video showing nice dribbling out the rockers. When I did the oil change, it wasn't particularly sludgy (but actually, the fuel pump was replaced because of leaky diaphragm)...

I never hooked up an oil gauge, just have the stock idiot light - ironically.
I don't know how to test if the main bearings are getting oil, but I do know that it's burning oil.

I'm so determined to get back on the road because she's just so beautiful.

Probably.
Cars and their parts deteriorate from prolonged non-use and from prolonged use.
They've got to be done…but given the oil burning, they've got to be done as part of a whole-engine overhaul.
Most of us don't; we have to farm it out.
No, that's not it.

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一期一会
Too many people who were born on third base actually believe they've hit a triple.

Well I got that, but the question is really whether just repairing the head would be enough for occasional light-leisure use (assuming we can restore oil flow without block work) and let it burn oil until perhaps the rings un-stuck themselves after some driving.

As for the head repairs, how much $$$ would you guess it'd land me, all said and done (machining, etc.). Even just a ball-park estimate from your experience
In my case, as much as I'd love to, it'd be too impractical given the money and accessibility constraints.
If not under already, I'd like to at the least stay overwater with this now-medium-sized project.

That (rings unsticking) is not very likely, but also not out of the question. How long did this engine sit before it was put back into use, and how many miles has it done since then?
Oof. I'm too many years out of the market to give even a decent guess.
That is a tall order. Old cars eat money! The days when a Dart or Valiant was cheap and easy to fix and keep in parts are pretty much in the past.

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一期一会
Too many people who were born on third base actually believe they've hit a triple.

The last head I had done (1year ago) I had the valves and seats ground. Reamed out the guides and installed bronze liners and sized them properly. Lapped all valves and re-assembled with new positive valve seals. $250 total. I did not need any new valves.

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2 Mopars come with Spark plug tubes. One is a world class, racing machine. The other is a 426 CI. boat anchor!

12.70 @ 104.6

It was sitting around 35 years in a garage on the east coast, up until around a year or two ago when I started working on it. It hasn't been driven more than a couple miles since then due to all the discoveries and the desire to avoid further damage. Plus, it's difficult getting around the block with 3 cylinders - even slant six and all!
I hear ya. I'd be curious how much value my Dart is worth as-is, at the moment vs. if fixed. As seen, the interior is in near-mint condition and I did much work. It's "just" the engine that needs attention at the moment.
That's comforting. What work did you do vs. what did the machinist do?

He did it all. I did a little bowl porting before I took it to him.

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2 Mopars come with Spark plug tubes. One is a world class, racing machine. The other is a 426 CI. boat anchor!

12.70 @ 104.6

Whoof! Okeh, well, you do stand some chance of freeing up the rings. I'd buy enough Kroil to put enough in each cylinder to submerge every piston top once the head's off, then spin the engine (5 seconds on the starter) every day, topping up the Kroil as needed.

Not really directly related, but It will also be a good idea to service the oil pressure relief valve to make sure it's doing its job, as described in these two threads: thread 1, thread 2.
Year, model specifics, number of doors? Odds are its market value doesn't change much one way or the other; best to think of it more in terms of usability and enjoyability to you rather than as an investment.

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一期一会
Too many people who were born on third base actually believe they've hit a triple.

I got quoted around $180 for the work as described (ground valves & seats, liners) by a reputable local machine shop (not including $160 dis/assembly).
Then, I reached out to a highly rated and fairy confident machinist who seemed to call that a total bluff and considered it major work (requiring new seat inserts for the unleaded, as Dan mentioned, etc.) - unwilling to go under $1k.

Initially I was happy to find a great price (closer to what Rick paid), but now I'm second guessing if he knows what he's up against (if it's such a big job after all)...
Anybody care to chime in on what to believe here?
Will absolutely do.
Sounds good. Will check it out.
1969 Dodge Dart Custom 225, 4dr, auto-trans, power steering, no A/C, tan leather interior
The key is, I’m working on someone else’s dime who's doing this purely out of generosity, and so I would like to keep this project within reason (they aren't as car savvy to relate to the costs) - but with an escape plan if the repairs don't work out.

This is way, way, way low. Beyond suspiciously low. Given the cost of parts these days, it's even suspiciously low pricing from buddy-who-happens-to-be-good-at-this-stuff-and-has-all-the-tools. Like, unless this is a buddy whose life you saved sometime in the past. Odds are much too great of this $180 and the associated time and effort going ker-flush.
That's more realistic. Consider: around 2012ish, I bought a top-notch street-engine head from Doug Dutra, which he built for me. $1,200 plus shipping. In today's dollars, that's $1,725.
Not from the factory, it didn't. Vinyl, yes; leather, no. Sounds like a nice car, the kind I like (high-trim 4-door 225/auto). Definitely not to be decided-about with regard to any kind of investment value, definitely in the "what will make it useful, enjoyable, reliable" realm.
Well, the repairs will surely work out, if they're done completely and competently.

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一期一会
Too many people who were born on third base actually believe they've hit a triple.