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Are you sure it happens exactly in the middle of the night? And what time is that anyway? 12:00 midnight? I don't go to bed until 11:00 PM sometimes. If I wake up at 7:00AM would the middle of the night still be midnight, or would it be 3:00AM? So please be clear on your query!

Thank You

EdTheHeaterMan.

SERIOUSLY Though.

I have noticed that some chimney down draft conditions can blow out a pilot. I had one customer with a standing pilot in a 200 year old home where the heater vented into an old unlined chimney. Upgraded the boiler to a spark ignition system but the water heater pilot would blow out occasionally. They were too old to go outside to light the pilot and had to call their 68 year old son to come and light the pilot. Also could not afford a proper chimney liner either. Only bandaid I could see for them was a CyclePilot that would keep sparking whenever the pilot would blow out. If the pilot relit within the 30 to 60 second window before the thermocouple dropped out, then the problem was solved. Every once in a while the weather was so windy that the pilot did not relight in time. But it was easier to relight with the sparker clicking away.

https://www.supplyhouse.com/Robertshaw-785-001-24-120-VAC-Automatic-Pilot-Relight-Kit?_br_psugg_q=pilot+relight

That's called a pipe radiator. It's missing the top, which is a cast-iron grille. Did you happen to get the name that appears on the base? I can't make it out…………………..

Looks like some flavor of a Bundy radiator although the catalog link seems to be missing:

Somehow I'm not that surprised… fixing a leaking valve stem can be really easy, or mildly difficult depending on how badly the valve is worn. The first thing to try is to get a good crescent wrench or regular wrench which fits the packing nut on the valve. That's the hex nut closest to the handle — the very "top" of the valve — and try tightening it. This is not a band-aid — this is what a plumber would do. If that doesn't work — don't be a gorilla — then you'll have to renew the packing. That's easy, too, but not as easy. Unscrew that packing nut completely (you will want the boiler off!) and remove the old packing which will be soft and torn up and between the shaft and the valve body itself. Get some new packing from the hardware store and carefully wrap it into that space between the shaft and the valve body and sort of push it home. Bring it almost level with the top of the valve body. Screw the packing nut back on and tighten it down… should do it. Be brave!

Note that many times the old packing contains asbestos so you want to keep it damp and contain it if it is white and fluffy or has white bits in graphite.

You can also just loosen the packing nut and shove a wrap or 2 of string packing in there and see if that tightens the old packing up enough to stop the leak.

In the laundry room it looks like a 3/4" pipe ?? coming off the top of tee where the vent should be. Maybe there is a vent up behind the ceiling. I would check that pipe out and see where it goes if you can. I may be tough to get a vent at the end of the main but it can also be drilled and tapped. I think that is the most important thing to do.

^^^^ THIS!!

You need vents on the ends of the main and the vents on the radiators checked. The boiler piping is questionable both in size and material but I think venting is your main issue.

In the laundry room it looks like a 3/4" pipe ?? coming off the top of tee where the vent should be. Maybe there is a vent up behind the ceiling. I would check that pipe out and see where it goes if you can. I may be tough to get a vent at the end of the main but it can also be drilled and tapped. I think that is the most important thing to do.

Also check the water level while it is steaming it should be steady or moving slowly up and down an inch or so. Violent fluctuations are not good.

Also what pressure are you running at? Should be 2 psi or less.

The Copper return line dropping out of the tee in the laundry room behind the washer/dryer….how does that get back to the boiler? Must be a wet return.