Currently, I am looking for flights from Siem Reap (Cambodia, REP) to Jakarta. There are not direct flights, so I'll need a transfer. Most options are listed as self-transfer (on skyscanner) which basically makes them just two separate tickets without any guarantee of making the connection.
Now, I can also book two separate tickets, a few days apart and spend some time in the city where I am transferring (visa I would need anyhow).
My question is: is there generally a price difference between booking two tickets at once via, for example, Skyscanner and booking them separately (with different airlines or dates)?