Best Of
Re: Return changes elevation and other oddities.
You're making it a good deal harder than you need it to be. The crossover trap I suggested takes care of the venting. The loop seal takes care of the condensate.
Now that loop seal has to be proportioned to the expected maximum steam pressure, or steam in the main will happily blow through it and get into the return. This you do not want.
Now you could also go the F&T route. A lot more maintenance and expense, but as you please. Be sure to use a small enough one — the usual error with an F&T is to make it too big. There isn't all that much condensate. Note that an F&T is NOT an adequate substitute for a main vent, so you will need to put a main vent at the end of that main if you choose to go that route.
Re: A 30 year water heater??
Canada will be the 51st state as of 12:01PM Monday the 20th.
Even the Burnham label makes stuff rot out!! LOL😊😊
Re: What saying or quote sticks with you since you were a newbie?
If you loan someone $20 and never see them again, its probably money well spent.

Re: Many years of issues with radiant floor heat.
If it is that infrequent, get an electric supplemental heater of some sort? Adding a few degrees to a 550 square foot room a few days a year for 8 or so hours should not be a big cost.
You mentioned a lot of glass, in the great room. do you have any sort of insulated shades to lower the heat loss through the glass? The more you retain, the less you have to deliver to the room.

Re: What saying or quote sticks with you since you were a newbie?
Except when you have to change a tire on a military four by four or six by six, right loosey, lefty tighty.

Re: Return changes elevation and other oddities.
I presume the dry return is vented somewhere? Like near the boiler?
More or less as @delcrossv suggested. Use that 3/4 inch stub, right angle to inlet of standard radiator steam trap, come out of the bottom outlet of that and down to the level of the dry return without that existing trap and drop. From somewhere convenient before that existing trap, go all the way down to the floor, come back up for your loop seal and tie into the dry return with the line from the nice new radiator trap.
Use the existing trap for a doorstop.
Re: Taco RMB not to use Nest thermostat?
as far as the NEST there known to have issues when Power steeling.

Re: A 30 year water heater??
My parents have a Richmond 30 gallon electric water heater still in service in their home from the original build in 1984, and a York 2 ton AC from the same date. Neither have ever been touched. Not a flush, not a new element, not an anode rod, nothing whatsoever. Meanwhile it seems every day I hear of somebody replacing a water heater that's less than 10 years old

Re: Best Code Protected/Keypad Lockout Thermostat for Single Pipe Steam? (or similar tamper proof)
I have mine set to 2 CPH which goes against Honeywell’s recommendation of 1 CPH for steam however after straightening out my main venting I began experimenting (3 was causing rapid cycling and I became concerned but when I went to 2 things smoothed out)
In my opinion and I’m sure some will disagree, but I am trying to balance comfort with economy and the 2 CPH keeps the house warmer and it runs about 20-25 minutes and shuts off, some may debate the increased cycles and it should run longer at each interval.
I have 3 remote sensors and they work great. I have setbacks as well and the t-stat stops the boiler just prior to reaching setpoint (3 sensors in average) to allow the room to go past the desired room temp.
