Best Of
Re: Oil Boiler Issues
Is your tank a Roth or a Granby? A plastic tank in a metal box? Is it square? I ask because if so, some of the suction line in those tanks were rubber and prone to collapse under a suction vacuum. Some even split causing intermittent lock out. With a Two pipe fuel system with a sound set of fuel lines one supplying and one returning to the tank it's unlikely a small amount of air would lock the burner out. These are just clues I'm thinking about. I'm starting to think there is an ignition problem. In other words, you are getting fuel and ignition for a week or more with no problem. So I doubt it's air in the fuel and more likely a problem with the ignitor. What kind of burner is it?
This is the point where picture are useful.

Re: New hydronic system
I agree and would recommend using an indirect water heater connected to the boiler. A much better setup than a heat pump water heater - especially if you have a gas boiler.
Heat pump water heaters are NOT the greatest.

Re: New hydronic system
Gas heat with thermocouple standing pilot boiler that you are happy with. If it were my heating system, I would not change a thing and hang onto that standing pilot boiler for as long as possible. Everyone I know has missed there's once they had gotten rid of it. I miss it too. Reliable, reliable.
If you are looking to do some homework for the future, and not wanting to do this right away. Getting rid of the B vent etc. A modulating condensing boiler should fit into your current boilers spot nicely. Especially if there is a outside wall there.

Re: Better to build pressure or short cycle gas boiler? Downfire?
" IF I'm starting to follow what your saying, you're also advocating for timers/relays - my comment was that with the provided controls I either need to build pressure or short cycle, I see that as either/or. Unless I'm missing something. Yes, with some added controls I can avoid the short cycling. I don't know the timing of the first cycle, obviously it also depends on how long the boiler was off/how cold it is outside. "
Yes, Very true. If you have to pick one I'd go with the short cycling.
However, IMO why would you leave it that way, when you can do better for not much money. Sure you could also replace the boiler with a properly sized boiler (no pressure and no short cycling), but that would be $$$$ and seems like a waste of money to me.
Re: Oil Boiler Issues
Is it actually losing the pump prime? You are getting air out of the oil pump when it is restarted? Do the oil lines come out of the top of the oil tank and are run overhead to the burner? You could have leaking fittings that are sucking air in but not leaking oil out. We see posts on this all the time
Re: Licensed and Insured !
Looks like they threw a pot of spaghetti against the wall and it stuck.
"Uhhhhh, Beavis…. huh-huh huh-huh huh-huh