Wholeheartedly, I agree that it's important to weigh the cost, time and goals factors into the equation.

Q: *HOW* secure does it need to be?


YASP = Yet Another Spare Time Project

Time is the enemy we all have to fight! That's why I suggested that you set it up as a multi-stage project plan.

Set a long term schedule, estimating time and costs and resources.


You had mentioned:
And digital sertificates is kinda hot these days, so it's gonna make me look good
So I assumed it would be new for you to deploy and therefore take longer than launching the 2nd machine. Do whichever option you "already" know and have the resources available to complete and get the users into production asap ... especially if this will generate revenue either indirectly or directly ... make it clear that further enhancements would be forthcoming. This meets production goals and gives you time for "professional growth".