Not sure why you would bother with Parallels. Aside from gaming, most PC apps either have a Mac equivalent, or there are other apps that can do the functions. Microsoft Office for Mac is quite good, including OneNote and OneDrive. Firefox and Chrome are also available on Mac. And, if you really do need Windoze for the rare occasion, BootCamp is included in macOS, so you can partition your HDD and dual boot to Win10 (don't bother with older Windoze releases). Or, if you have the space, keep the PC for the rare occasions. At work, I have a Mac with 2 24 inch monitors, and 2 PC with 1 24 inch monitor each. Using an inexpensive app called Synergy, I am able to navigate across all 4 monitors using a single mouse and keyboard with the mice and keyboards for the PC tucked away for the occasional login\reboots which require a directly connected input device.
I dove into the Apple ecosystem in 2010 following a couple of years with iPhones. I use Mac exclusively at home, and at work I manage dozens of Linux, Windows and Mac machines. My iPhone and iPad seamlessly integrate with the Macs, and I have AppleTV at home and work for airplay video and audio to big screens, again with very little fuss.
For newbies, there are plenty of helpful blog and forum sites that are a google away to help with any questions you may run into. Apple even has a good online guide that is targeted for PC users who are converting to Mac.
But, for me, the biggest selling point with Macs is the "It just works" factor. I find myself constantly updating, battling malware\virus, and tweaking PC to get them to behave. Macs have a few updates every now and then for security patches, and a new OS comes out annually with new features...at no additional cost and applying these are as simple as Windows Update!
Unless you have a burning need to be on the cutting edge, any 2011 or later Mac should give you the tight integration with iOS for a few years. Macs tend to have about a 5 year life, not in terms of hardware but in terms of support from Apple. Sure, some of the newer macOS features will only work on the newer Macs, but these are generally not essential for day to day use. So, to overcome the planned obsolescence factor, stick to a newer model.
The latest models are adopting new connectors, and that may prove a bit of a challenge. For instance the MacBook and MacBook Pro now use USB-C or Thunderbolt\USB-C ports for power and external connections. You might need a dock or adapter to connect legacy DVI or HDMI monitors, and legacy (USB2 or 3) USB devices, etc.