Best Of
Re: NEW STEAM BOILER COST
Much more than twice the retail price. Domestic iron piping is quite pricey and slow going.
And Labor rates depend mostly on the cost of overhead where you are. There you get what you pay for.
And if you can afford it, you should look outside the boiler room and correct any problems that hacks and time have invested into the system: Old mismatched painted radiator vents, leaking valves and ancient rusty wet returns. It may be the first time anyone's putting work into the system in eighty years.
Re: Vent Problem on One Pipe Steam System
Vents won't affect water hammer, nor help you here. I don't particularly like those main vents you chose but they might work OK.
But for now forget the vents.
What happens to the water level in the gauge glass when you are making steam?
I suspect you are surging due to the insane boiler piping and probable bad water quality.
Re: NEW STEAM BOILER COST
Frequently more than 3X when all the piping and controls are considered. The boiler itself is not all that costly.
It's the labor and all the piping and controls that really add to the final cost. Could be 4X if the job is done really well with a drop header and generous sized piping (NOT 2"!!)
It takes 40-48 man hours to properly remove and install a new steam boiler with all associated piping and controls and startup and some skim. If it is not planned perfectly, with every possible needed pipe and control, the number of man hours climbs from there because it becomes multiple trips to the supply house(s)
The price per hour is depending on where you are located. Make your own estimate and calculate the total labor.

Re: DIRECTION OF STEAM TRAVEL
The amount of wrong near boiler piping versions out there is amazing.
Re: unmarked radiator identification
That looks like a standard thin tube or "slenderized" radiator, which came into production around the second world war. It should be on most of the usual radiator sizing charts.

Re: Steam Mains Insulate or not?
The president of my Coop removed about 13 feet of insulation in our basement meeting room to warm it up. The result was the steam took about 8 minutes to reach the 5th floor instead of 6 minutes. I put it back. I can't tell you what will happen in your situation. There are wall and ceiling radiators that can supply heating in those situations. The money and persons to install them may be a problem.
Good luck