Rebuild or replace?

Still having issues with the cooling on my 67 Dart GT convertible, 273 4bbl, 904, 7.25 3:55. Still getting way too hot on 20+ mile runs, and burning oil. Pretty sure there is corrosion in the block that’s preventing flow, and likely a head gasket issue (some oil in the coolant).

Torn between seeing about having the 273 rebuilt (to the 273 Super Commando 275 hp specss) or getting a 408 stroker with about 400 hp.

I assume a pull, rebuild, and reinstall will run me around $3.5-4K ish, while prices on crate strokers seem to be right around 6k for just the engine, no labor.

Car is just a weekend cruiser, but is also dreadfully slow as is. My mechanic described the engine as “tired and worn”.

Guess the big question is whether the rest of the components will handle a stroker, and if changing to the bigger engine would increase or decrease the value of the car?
Your call on that one. Been there, done that. I rebuilt my HP 273 in my 66 Dart. I have no regrets but I have a healthy sum wrapped up in it. It runs good but a stroker would be more fun for about the same money. Buy an engine and park the original in the corner. It could always be freshened up and put back in if need be. Use your valve covers and air cleaner to make it look like the ol' 273. FYI there was never a "Super Commando 273". The 275 horse engines were built for the 1966 D Darts only.