"Cutting-the-Cord" may or may not be difficult. It all depends on what you want to go with. I have been using Roku's for several years now and haven't looked back at cable. However, Cutting-the-Cord can have different meanings to different people. When I started off, I relied entirely on my local media to play content to my TV's using Plex/Emby and my Roku's (I still use this setup to this day). There was no YoutubeTV/SlingTV or any of those apps we see today that provide live content. I subscribed to SlingTV and then moved to YoutubeTV because I like sports, and my kids like watching their shows on CN, Disney, etc.....
So did I really "cut-the-cord"? It's more like I migrated to newer technology that gives me the ability to pick what I want to watch. But in the end, with the amount I pay for a 500 Mbps download speeds (I game a lot and work remotely from home at times) and for YoutubeTV, you start to get close to cable subscription pricing. You can save yourself some cash by going with lower speeds, but it all depends how you use your network (4k content, 1080p content, streaming?) This also goes hand in hand with your current networking hardware.
So you have to ask yourself: Can I do without live TV or premium shows at all or do I want more control on the content I watch? "Cutting-the-Cord" is very misleading. It's more like "Upgrading-the-Cord". Your just getting your content in a different form, but still paying for the content.
And btw, Geek Squad are the worst, especially if you are non-tech-savy. They will milk you for your cash. Don't go with them. I don't understand why some tech people recommend them. They'll rip you off, seriously. Just research and use the net to get familiar with non-cable tv setups.