[joosttx]

Is custom steel the way to go or too heavy?

I would argue its not worth the price for the benefit you get.

Is it really any fun to ride a gravel bike with road wheels on road (not for racing or anything but still 30-50 mile rides)

Its fine but if you want to go fast like in a fast group ride you will be at a disadvantage.


Do I need two sets of wheels for on and off road?

No. Gravel on the east coast especially in the MA you can ride on big road tires (30/32mm).


If I want disc brakes, Sram, and 1x11 what’s a reasonable price range?

$3-5K.

Is there any point in looking used?

Yes.


I don't know your price point or fitness level etc. But judging from my experience riding the gravel roads in New England you can get by on 30mm tires. Descents maybe a little scary depending on your handling skills. I rode a D2R2 on 28's many years back and was fine. I would of preferred wider tires but 28s were manageable.

If I were you I would get a nice carbon road-ish gravel bike or a nice carbon road bike that can fit 30-32mm tires. I think these are your two choices of bikes and you know better which one you do you best. Good luck and congratulations!