I tried dual booting, and I found it to be annoying as well. I always had to reboot because something I needed was on the other OS. Over a few weeks Linux was just taking space on the drive.
More recently what I've been doing was to run Linux in a VM that starts automatically on full screen when opening my Windows session (easy to set up). So now I can work with both in parallel, transfer data, synchronise clipboard with Ditto, have my Windows-specific software while still using Linux as my daily OS. Even better now since I have a NAS which I didn't have during the dual boot period, so I can mount drives for both. For that you can either use VMWare Workstation Player or Oracle VirtualBox, they're both free.
When it comes to swap, of course you will be able to run Windows in a VM on Linux. But transfering your current data ? I'm not sure at all. It might be doable, but I think you should save your data externally for both machines and do a proper reinstall. It will save you some time and hassle.
Well that's my main issue, my rig runs an i5-6900 and I have 16GB RAM. I gave 6 to the Linux VM, and try to maintain the usage on Windows as low as possible : not having the browser running on both, a plug-in to put to sleep tabs not used, stopping processes I'm not using. KDE is a bit too much in my case, but Cinnamon, or XFCE are working fine. I've found a new love with i3wm but it needs some time to tinker it to your taste.
But if you have a more recent computer, you should be fine. Upgrade the RAM maybe, if you find it to slow.