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It’s going to be a balance between your time getting an automated approach to work and the cost/effort of getting a monitor. Getting preseed working can be a bit fiddly, but it does mean you’ve learnt a new skill, getting a monitor sounds like it’ll be a pain, and you might only need it once.
Putting a simple preseed file on a debian install image is probably going to be your best bet. Assuming you can run a VM on your current machine it shouldn’t be too difficult to test it until you’re happy with it.