If you own more than two silicone toys: separate bags, before anything else on this page. Silicone against silicone reacts and goes tacky, and it does not come back. This is the cheapest problem here to avoid and the most expensive one to ignore.
If you are buying furniture for the first time: a wedge. It stores under a bed, it solves the most common complaint, and it tells you quickly whether the bigger pieces are worth it.
If discretion is the point: buy for what it looks like closed, not open. A neutral wedge reads as a cushion and a lined travel bag reads as a wash bag. A stool does not read as anything except what it is.
If you travel: the bag matters more than what goes in it. Hotel drawers, shared luggage and airport security all get easier when everything is in one lined case that closes properly.
On what lasts: removable washable covers and wipe clean linings. Foam and fabric both outlive their covers, and a cover you cannot wash is what ends a piece well before the foam gives up.