If great-grandpa’s taxidermy collection or grandma’s crocheted toilet paper cover make you cringe each time you dust, they aren’t contributing to fond memories of the individual. Do you have other, more meaningful reminders of that person?  Keep only those things really add richness--would that person want to be remember by something you consider tacky?.  (A sidenote here: It is always a good idea to take pictures of any mementos before passing them along.) 

If you are saving things for your children, talk to them about the items now so that they will have a connection.  Write down why you have saved certain treasures.  A scrapbook of photos of family heirlooms and and the stories behind them would be a blessing to inherit and lend meaning and a heritage to the objects.   I recently put little notes on the back of a few pictures, inside vintage books and on the back of an heirloom plate to keep the history of these items alive.

 

Parting with a gift can also be difficult. Evaluate honestly whether the giver would want you to keep the item once it was no longer useful to you. In some cases, yes, the giver would be hurt, and that is something you can factor in. In other cases the gift was purchased to bring pleasure for a time, and the giver would not want it to overstay its welcome. 

Is it a duplicate? Sometimes it pays to have duplicates.  Honestly evaluate whether each stockpile is practical.  Sometimes it can be more cumbersome than convenience and more waste than thrift.