IMO/short rant:
Linux works f*** great. Really great. Huge strides have been made to make things user friendly.... but at its core its still made by a bunch of nerds. Utilities are often made CLI only at first, and nice useable interfaces are made as time allows.
Linux is so versitile, I find it can be hard to find distros that work well out of the box. Most work 99% but basically all that I have tried have eventually had at least minor nagging issues. At that point the premade distros are harder to fix because they are not nearly as transparent.
/rant
IMO there are two styles, and if your technical and hands on I kinda urge you to choose the second.
First, finished distros like mint, ubuntu, ect I find to be like a modern car. Everything should just work, and you are not even supposed to check your transmission fluid. Pop the hood and you only see as plastic covers. As long as everything works your gold, but if there is an issue its probably with one of the convoluted "solutions" they provided you.
Second, distros like Arch (I am bias and run arch on everything, lol), or gentoo... Not at all for everyone, you basically have to install and configure every component of the system yourself. This is like a 70s car. Grab an adjustable wrench and some duct tape and you can fix ANYTHING in an afternoon. No extra parts and whats there is pretty simple. Arch at least (gentoo too) makes this "easy" with the most insainly amazing documentation and step by step walk through I have seen anywhere (not just computers)
I bet you could do that second route pretty easily judging from you last post...
And yes, you can do something like modload...
https://wiki.archlinux.org/index.php/Kernel_modules
MOD, are you familiar with xrandr? basically the stripped down way of dealing with multimonitors. It will tell you what monitors are attached and allow you to set what ones are active, how they are sized and where they are located... check out
http://i3wm.org/docs/userguide.html#multi_monitor its from the i3 window manager docs, but gives good examples of the xrandr command at work...
Wine
Hit an miss? Your probably screwed on your visual studios. Can you adapt to another DE? If your working in VB you probably wanna stick with windows, at least on a virtual machine inside linux
otherwise what about eclipse? Similarly with like outlook, ect... do you really NEED these, or could you make other alternatives work? Part of using linux will mean a new set of tools.... You will be much happier if you can just find a Linux equivalent instead of trying to pretend your still on windows.
Make sure you check out:
https://appdb.winehq.org/ , they keep a database of how well programs work in wine that is fairly extensive (as well as sharing info needed on what additional components need to be installed)
Multimonitor - see above... I think most desktop environments use their own tools to interact with you and automate monitor setup, but on the backend I think they are all just using that xrandr utility to tell the kernel whats attached, as such they should all work decent. Perhaps there will be some differences in how pannels or widgets are handled in a multi monitor environment.
Windowing/DE
Your wrong if you don't use only a tiling window manager.
(have we established that this part is my opinion?)
DE's-
XFCE4 is an old one, and can look like it.... Especially with a default install.
Mint makes it look a little bit nicer. Super stable however, very well supported and with enough work can be made to look REAL nice. Great lighter weight option with lots of features.
Cinnamon is nice, and fairly fancy... but IMO too young. I used it for a while and if you want a basic DE that looks nice its a decent choice. I don't think its AS stable as older options
Mate is a fork of gnome 2, 3 was too big of a change, so people maintained the old one... Its nice. Not as polished looking as Cinnamon, not as supported and expendable as XFCE4, but maybe a nice middle ground if your not trying to do anything crazy but want lighter weight then cinnamon.
Unity is OK.... but its own style... and heavy. If I was using a DE I would prefer closer to a windows paradigm? I feel like unity reminds me more of mac?
KDE is great. Heavy. Learning curve too... I had to google how to change my desktop background, lol. Hugely customizable, good stability, very modern... I think this is my choice until I realized that a DE is just a buch of crap I don't need taking up resources, and I don't care what things look like...
WINDOW MANAGERS-
You only really need a window manager
Nice because its very lightwieght and very basic.... But you get nothing other then a way to handle windows.... So if you want a panel you will have to download and run one separately... if you want a battery status you will need to handle that separately, if you want wifi status/dialogs you need that separately... Most will have some forum of system tray though so you just need like nm-applet for instance to add wifi status, or xfce4_power_monitor for dimming options, ect...
i3 is what I use, its a manual tiling WM. Basically when you have one window open its full screen. When you open another application, it will split the screen in half. You can choose horizantal or vertical, as well as resize the split between the two windows. You can then split one of those windows in half, ect... so no windows overlap, they all tile and take up the full screen with 10 virtual desktops. LIGHTWEIGHT. once you have X installed on your system, i3 is like 3mb, vs ~300 for a typical DE. You DO have to run a program to set a background if you want one though, otherwise it will just be black lol.
Awesome WM Does the same thing, but tries to dynamically resize the windows. You choose different layouts and it will automatically do one window taking up the full left half of monitor, with two windows split vertically on the right (or what ever other of its handfull of layout options you choose)
Openbox is good if you want a more typical desktop.... good for basic window control, drag them around, minimize, maximize, ect...
Live CDs are great though. Get a USB drive and start flashing different distros. Then boot up and try for a while...
Debian is crazy stable but typically older software avalible from its repos. They are not in a rush to get new versions they may break.
Ubuntu is a debian derivative but with newer repos... and canonical. I don't think they are really with the spirit of linux anymore... They just want to monetize and be their own thing... Decent base for other distros though.
Mint is where I would send someone who doesn't want to do computer stuff, but wants to use linux
Arch installs only a basic system with a command prompt, no graphics. You then build out exactly what you want. You have to pay attention, and modify configs... But all the software tends to be bleed edge and some how this is still the most stable distro I have run by leaps and bounds (likely do to the fact that I am better at it, because they teach you a lot more, because you HAVE to know more to use it). Nice part here is you can just uninstall your desktop environment and re-install an new one. Lets you test what you like pretty well as you don't need to re-install the base system to almost completely change how you interact. My laptop has had basically all the environments I listed here installed and unistalled at one time or another, with out re-installing OS. Basically any linux can do this, but MUCH easier to do on something like arch.
Gentoo is similar to arch. I don't think their documentation is as good. It is interesting in that all programs installed are built from source on your computer... So if you want to geek out and setup build flags, everything will be built for YOUR computer and will likely work very well.
SUMMARY:
Basically Arch for hands on (feel free to shoot me an email if you want help with that), or Mint for just works (hopefully)
XFCE4>Mate>Cinnamon>KDE
Going from lightweight to fancy
Sorry... I wrote too damn much.