My end of chain needs: Does this pedal exist?

I was looking for a pedal like this and couldn’t find exactly what I wanted, so I built my own. I didn’t total up the costs, but I’d guess around $100. It has everything you asked for (including optional features), but it’s big and ugly :)

It also has an aux input, a fixed boost, and an adjustable cab sim that ranges from soft/warm to tight/forward.

Happy to provide a schematic if anyone wants it.

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Is this based on something?
 
I kind of view headphone out jacks as something that comes after other features. So if a preamp has a headphone out jack, it probably has a whole host of other stuff going on. I could be wrong though.
I take the XLR out of my preamp into an audio interface and monitor with phones through the interface. This might be a more accurate representation because some preamps will bypass or add certain things for the DI out. As an example, the volume control on the Noble preamp doesn't affect the XLR out. I thought I saw another piece of gear where the cab sim is only going to the XLR, not the instrument out. Etc.
 
I was afraid this might be the case…

You are so right. It seems silly to spends $300+ on something of which I only need two features.

The main reason I want a box like this is because I’m mostly playing live, and I want to have an accurate understanding of what I’m sending to FOH. Currently I am using the headphone out in my Fender rumble… but I think the rumble is adding some color to the signal. So when I set my tones and then go to plug in to the system, there are usually some major differences between what the rumble gives me and what comes through the PA.

I know that headphone Vs PA will sound very different. But I can at least get rid of one variable using something on my board to practice rather than using the Rumble, which is omitted in my live signal chain.

My advice (which is probably not what you want to hear): This is a really bad idea. Leave the mixing decisions to the FOH engineer who can actually hear what's coming out of the PA.
 
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I am tempted just to use this… but aren’t they notoriously unreliable?

I use an Element for the exact scenario you are describing, end of chain DI, headphone amp, and cab sim. Haven't had any reliability issues with mine, and can't say I have heard of any TBH. I would just buy one of them because it meets all your requirements. If there is an issue, return it on warranty and get a replacement.