You obviously love your Ollie very much and want him around as long as possible. As others have mentioned, going outside is dangerous. It is a controversial topic but it has been proven that a cat does not live as long due to predators, nasty neighbors, not to mention cars. A dog is not put outside expecting to come home safe and sound - a smaller animal like a cat should not be either. Also, fingers, ribbons and strings are not great toys. I am speaking from experience as I have been with rescues and shelters for many years and have always have cats of my own. Jackson Galaxy (My Cat from Hell) agrees on all I am mentioning above. Using fingers as a toy could result in serious infections for you due to a cat's saliva (or a visitor). Hands are for love, toys are for play. Ribbons and strings can choke easily due to the tongue your cat has - it will just keep drawing the string or ribbon in and they cannot get it out of their mouth so it is best avoided (elastics also very dangerous). Just trying to help avoid any sadness in the future. Take care!