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I would say as long as you get a monitor with Display Port, you'll be fine. If you plan to do dual monitors, then make sure your monitor supports Display Port daisy-chaining. Basically, it will have one DP for "in", and another for "out".

Scaling is an issue from time to time, you will find tons of comments about it. The biggest issue that seems to affect people is that after they dock the Surface, they sometimes have to sign out and then sign back in to get all the displays to sync properly.

But definitely, if you have not purchased your monitor yet, then get a Display Port monitor, and keep your connections from dock to monitor native.
 
Asus VE248Q - $169.99 (after $20 rebate) on newegg
Acer V246HL - $169.99 on newegg

I use an Asus 24 inch monitor (it doesn't have a display port), but I have found through research and use that Asus delivers great quality at a reasonable price.
 
I have 2 U2414H's from Dell daisychained together. Works great. I had some issues with scaling before the last big monthly update. Since then I haven't had the issues. I also have my 2 montiors being used without the surface screen. So my surface either has it's touch screen or the U2414's, but never both. I think that helps vs. 3 displays.
 
I have my Sp3 connected via hdmi and it works great, no scaling issues and my monitor was a $129.99 Asus.
 
I have 2 U2414H's from Dell daisychained together. Works great. I had some issues with scaling before the last big monthly update. Since then I haven't had the issues. I also have my 2 montiors being used without the surface screen. So my surface either has it's touch screen or the U2414's, but never both. I think that helps vs. 3 displays.

I'm looking at the same setup as yours. Are you saying that with the two Dells attached, your SP3 screen isn't available when docked to the displays? Please explain.

Also, am I correct in that I should put the SP3 into the dock and do all of my updates prior to use to make sure all drivers/firmware load properly without added issues?

UPDATE: I found the steps to fix the disabled SP3 screen in this scenario in the thread daisy chaining surface pro 3, SP3 screen disabled.
 
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I'm looking at the same setup as yours. Are you saying that with the two Dells attached, your SP3 screen isn't available when docked to the displays? Please explain.

Also, am I correct in that I should put the SP3 into the dock and do all of my updates prior to use to make sure all drivers/firmware load properly without added issues?

UPDATE: I found the steps to fix the disabled SP3 screen in this scenario in the thread daisy chaining surface pro 3, SP3 screen disabled.
I also have 2 U2414H daisychained together off the dock, and routinely run both + the SP3 screen all at once.
The first week I had them they were a bit flaky (flickering on the last one in the chain), but I found that forcing the display refresh rate to 60Hz (they autodetected at 59Hz) has made them rock-solid. They make for a nice multiscreen setup with the thin bezels.

That's the good news on hardware covered - I'm less happy on software. SurfDock is right about the DPI stuff : I just can't get the display scaling to work to my satisfaction:
  • Provided I set one of the Dells as the 'Main Display', they scale OK, but the SP3 screen has any desktop apps smaller than I like, and blurry.
    As a result when docked I tend to use that display for ModernUI only.
  • I find I always need to log out and in again after docking to let the scaling 'settle down'
  • About once a week I will dock and Windows just refuses to fire up the monitors. Actually needs a full power-off of monitors at the wall to bring right.
 
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