So if you replaced the 220R (R3) and 270R (R2) resistors with 500R that would mean you are only sourcing less than 5mA instead of nearly 10mA for the MIDI out.
i.e. 5V (from game port) - approx 1.3V (optocoupler Vf) = 3.7V.
3.7V through 1000R total (your values) is 3.7mA.
3.7V through 490R total (original schematic) would have been 7.5mA.
It is a long time (30+ years) since I made any MIDI projects, so I checked the MIDI spec and it says a minimum of 5mA.
Depending of the optocoupler in the Roland synth, the Vf might be higher and your changes are just not generating clean enough transmissions at 31250 baud.
I recall having a bunch of optocouplers back in the day that just couldn't cut it for MIDI, but back then I relied on getting most of my parts for free.
You can easily make lower value resistors by paralleling a couple of them e.g. two like values to get half the value, such as 2 x 510R in parallel gives 255R.
I doubt the 220R or 270R values are at all critical, but doubling them seems far too much.
If anything I would just remove R2 completely if you don't have C1 and C2 installed, and with R3 of 270R to get about 13mA or a max of 510R to get about 7mA.
Oh, and where are you getting 500R and 2.3k resistors? They are not in any of the normal preferred values, even the E192 series.