First, my suggestion: "Protect Tittlebars"

I'm running Windows 7 Pro x64 and DF 7.1. I'd love to see a feature where DF monitored if windows' titlebars were UNDER the taskbar. I have my taskbar at the top, and it is locked, but Windows by default is not smart enough to realize that it opens some programs with their titlebars UNDER the taskbar, making ease-of-grabbing and dragging the window/app difficult.

Secondly, I think "Window Location"is broken. Ideally, I'd love to see a feature in DF that is similar to Divvy (http://mizage.com/divvy/) It's a window grid system that works great (when it works) since I have 2x 27" 1440p monitors, and I'm very particular about the placement of my windows. But on to the issue.

I go into WINDOW LOCATION, check the "Enable Window Location..." option at the top, click ADD, select Google Chrome, and set it to "Move to Selected Monitor" and choose #2 (after verifying that #2 IS the right monitor). So, each time I open Chrome, it religiously opens in Monitor 1, and I have to middle mouse click the titlebar to move it over to the other monitor.

Am I doing this wrong, or is there a way I can better ensure that I can have windows open on set monitors at their current dimensions? (I could use Divvy to position/size them, but then it'd be great if DF could save their position and ensure they open like that next time).

Try this:
Right click tray icon, and select Monitor profiles>Create/edit
Then click the Splits and padding button add a vertical Split
Set the height to 40 (might need to adjust a little for your taskbar)
Then hit OK

UPDATE:

Seems that didn't resolve the issue. Now I have problems where SAVE AS modals and other instances of windows open in the "32px high" split, making them nigh-on invisible, or hard to manage.

Eh, it was a shot in the dark, and not the intended purpose of splits , You could also try a program called 'desktop coral' (its freeware) and its actually more closely designed for what you intend.

Good "thinking outside the box" skills there, no doubt.

Man alive, though, am I right? I'll have like 4 window management tool running just to get the OS to do something it should have been doing out of the box. I think of all the outstanding issues, getting the apps/folders to open in the same place at the same size is the next biggest problem to address.

I found out that for hidden titlebars, I can quickly press WINDOWS KEY + ARROW UP/DOWN in order to cycle it through current state to full/min (at full size I can grab its titlebar).

Nonetheless, I appreciate the info!

Sadly, the only thing stopping me from making a COMPLETE jump away from Windows operating systems is my love of gaming. I find it ridiculous that a company who has NO interest in PC gaming (but loves to SAY they do), to still be the king to hold the crown in that field. But it'll take a push to OSX/Linux from major players AND a shift in the field to develop games on *nix platforms primarily before this happens. Still, one can hope. I have a MacBook Pro and I love that OS.

It is ridiculous for you to need an obscure workaround for a bug that micro-soft should have fixed ages ago.. but thats life because they dont have much competition (until linux can natively run windows executables, without the user having to work for it with wine)

I hear ya. Would not be at ALL surprised if Microsoft's Windows 10 did not address the issue. Hopefully I'll find something. Divvy is nice as far as quickly gridding my windows. And some apps (Chrome) are smart enough to remember their location/size. But others like Cygwin do not. They open a set size/location no matter what.