Best Of
Re: Rebuilding old radiator valves or replace?
What's wrong with the valves that you need to rebuild them? Or do you just want to? If it ain't broke…
You are missing something with the new steam valves: you also have to replace the spud in the radiator, which usually is no simple task. Further, the chances of their having the same dimensions (height and offset) as the old ones are exactly zero, so you will find yourself either moving the radiator slightly or the pipe — which also may be a little more involved than you think.
Re: Any device to prevent high wind from blowing out the WH pilot light?
For what it's worth the house I grew up in had an atmospheric furnace and a water heater that fed into a masonary chimney. Over 40 years the pilot never blew out in either of them and there was no cover on the chimney.
The chimney extended above the ridge of the roof by 3 feet or so, and then the terracotta clay extended a few inches above the brick.
So what, why am I saying that?
Apparently that arrangement works under most conditions. And I think it was already previously mentioned, but the draft hood should prevent such problems. I'd patch up that chimney and fix the leaks etc because they are going to bite you over time and it's going to be bad, but I suspect you're going after the wrong thing. Like you said, the previous tank was fine for years.
I'd pull the cover off of the heater and look at the pilot to make sure it's burning good and it looks like a reasonable sized flame etc.

Re: Steam Mains Insulate or not?
Im a BIG believer in insulation. However. Removing some to create a living space that works best for you is fine.
Make sure the insulation is fiberglass and not asbestos. If its fiberglass remove it yourself. If it's asbestos you should have a remediation company remove it, and have it removed first before remodeling. It can make a big mess.
Steam boilers need a mechanical room/basement for maintenance. Do not build your boiler in so tightly that when service is needed it will make a mess of the adjoining room(s). Not to mention your boiler needing the proper amount of air to function safely. People have died from building things too tightly. Suffield Ct. comes to mind. Many a rec. room has been ruined by having a boiler in an adjacent room.

Re: Furnace playing games
The R8184G could have bad contacts. If it wasn't in safety, but just lightly tapping it by coincidence started the burner, I'd say that's likely the case.
The R7284U is an easy upgrade. Just make sure you program it for no pre or post purge if there's no oil delay valve.
And FYI, oil burner service is not DIY. "The flame looks good" doesn't cut it.

Re: A shout out
I remember Bond Bread deliveries, also milk in glass bottles and Cushman Bakery all delivered to the house.
Gas was about $.15/gallon and Cigs were $.25/pack.
The good old days.
Re: Common issues (low hanging fruit)
I'm not a heating pro, but I learned from the pros here that our Weil Mclain cast iron hot water boilers should have been installed with bypasses for protection against low return water temps. Since then, as I've read installation instructions for cast iron boilers from other mfrs, it seems that virtually every cast iron boiler mfr requires a bypass for return water temp protection. And it seems many cast iron boiler installation pics posted here by homeowners with problems lack the required bypasses.
So it appears that many installers commonly ignore the mfr's bypass requirement for cast iron hot water boilers, either because they don't read the manual or because they know the customer won't know the difference.
Maybe these are the same guys who don't read the manuals when piping steam boiler headers. 🤔

Re: strong smell after boiler install
My knowledge of physics is really quite poor. But I would think the following. The cast iron is what is heating the water. In order for the cast iron to heat the water to 212, I would think that the cast iron needs to be significantly hotter than 212.
Re: Electric heat is too expensive, very high bills/useage
@bjohnhy has a good summary.
The biggest issue is with air leaks. I'm in the land of 2.5 story houses and after the recent snow dump, all the older houses have sever ice daming issues. That is all from heat loss from air leaks into the attic space melting the snow on the roof.
Most would be around 15 ACH@50PA (aka, leak like a sieve). Your local energy company might offer reduced rate or free blower testing as well as air sealing upgrades. Worth it just to see where you are. The good news is most of it can be done with elbow grease. The bad news is that it is very unpleasant work to do inside those tight spaces.

Re: Common issues (low hanging fruit)
I would say pipe size and pump selection requires no more experience than the things you mentioned. less in my opinion because its fairly intuitive to someone who knows nothing about hydronics that pipe size and pump selection must matter because there are different pumps and different size pipes so a novice who knows nothing might think to check these things. Quick rule of thumb references are available freely and easily with a google search and will serve most jobs adequately. 20 minutes or so reading about it and you are able to crunch the numbers yourself. For simple residential jobs this stuff is very basic level stuff, the most basic really.