Using Bridge to add Key Words to specific locations on family videos.

Bridge Newbie here!
I have several hundred hours of family videos captured over 3 decades, that have been professionally digitised (and therefore don't require much further editing to cut out problem areas, etc.) and are now stored all together in the Cloud in 3 main folders each containing over a dozen files. Most files contain 3 hours of video.
What I am hoping to achieve is to create a bunch of key words - e.g. Country, year, activity, family members by name, etc. I will then watch each clip in the preview panel and as the video plays click on keyword(s) that are relevent to that portion of the clip. For example, if my son Peter is on the video from 14m 20s to 16m 5s, then I click 'Peter' on at the start of this segment, and click his name off at the end.
My question is this, if I subsequently search for (say) "Peter" + "Italy" + "1997", will all the clips that meet these criteria be correctly filtered, and if I click any clip, will it start playing at the relevent point in the clip?
What happens if there are several segments in one video file that all meet the specified criteria - how do you choose whcih segemtent to play? If Bridge doesn't offer this functionality, any suggestions as to an alternative? I don't want to purchase an application or software that has huge functionality and a steep learning curve, when all I want to do is whay I describe in this post. Thanks for any advice.