The "Windows issue" is applicable to previous scanner models, (pre 436/536/SDS100). Those model scanners use a USB programming cable. The previous scanners (x96) used serial cable which could present issues (unless you had the right kind of cable).
I looked and confirmed the Greater Cleveland Area Radio "stuff" requires a scanner capable of receiving digital.
https://www.radioreference.com/apps/db/?sid=7337
The 436/536/SDS100 scanners are capable of monitoring this system. They can almost be used right out of the box by entering your zipcode and selecting the desired service types. (You probably would want to update firmware and database for best results, however).
Creating Favorites Lists can be done to refine scanner choices, but they require learning programming software.
Presuming I'm the typical scanner user, I too struggled with programming at first. The more I did it, the more comfortable I became. It's about like anything new - difficult at first, not too bad after you get the hang of it. You probably will make mistakes at first - we all have. No scanner was ever ruined by bad programming. You can start all over if needed.
With all that said, a little potentially bad news. Cleveland is a simulcast system (several sites/towers transmitting on the same frequency to ensure coverage). The x36 scanners have been known to have issues decoding signals of this nature and people hear either nothing or garbled audio.
This is sporadic, however. You could be in a bad simulcast distortion area, or you could be where it isn't a problem. There is no way of knowing until you try it with a scanner. Perhaps you know someone in the area that can give better feedback on this.
The newest scanner, the SDS 100, is much better at simulcast distortion, but it is more pricey.
