New to Mopar

Question...will '73 "587" heads fit comfortably on a '69 273?

After reviewing some answers (thanks guys), looks like the "587" heads will not fit comfortably on a '69 273.

Obviously, I can't attempt to treat this '69 Dart with the original 273 / 904 with a noisy 7.25" like a '67 Nova. I have to make some real decisions here, with an attempt to wake up this 273. Engine is OK, however aged with it's 2V. I was hoping to pump the HP to somewhere near 300. May not happen with this small of engine. I can pull near 400 easy enough out of a 327, Mopar seems to have disposed of the 273 in place of the mighty 360. So, it looks like an engine swap is my only real alternative? Help!

Let me please ask one last question of you guys. I was at the Goodguys car show in Pleasanton, CA today and spoke with a guy there about his '69 Dart, and picked his brain about my dilemma. His car has a 340, and he (obviously) swears by that engine, which I can understand. He too was plugging the 340 and 360 as most guys who own Mopars do. He also poo poo'd both the 273 and the 904, and advised me to install either a 340 or 360 with a 727. At one point I asked him value wise, which would be the better resale value...the car with it's original 273 / 904 or an installed 360 with a 727? He jumped right away with the value being greater with a 360 and 727 transmission. I don't want to be too attached to the originals if with the same amount of work and cost I could generate a more valuable car. Those who gave me the best responses to my previous question, can you please tell me what you think about this. Glenn P.S. I found only 4 Mopars at this entire show. It was more of a Chevy fest than anything. But I was lucky to find this one guy with a car very similar to what I'm trying to achieve with mine...a good looking, head turner Mopar, that also has plenty of power.

As you know everyone has their opinion. The nice thing about Mopar cars is they can be made to run and handle sweet using stock parts. The 904 is no problem. You can change the fluid and filter, replace the 2nd gear band lever to the 4.2 that the 273 Commando used BAND LEVER - A&A Transmissions , adjust the bands, and up the pressure while you have the pan off. If you do not have partial kickdown you can add that also through A & A Transmissions, 727 3-2 Kick Down Module (1966-69) - A&A Transmissions . Make sure you can adjust the kick down when you swap to the 4 barrel carb. Try this first before you get a convertor. What brakes do you have?