@Yoyo3 It would be a bit spoiled and entitled to expect the homeowner to come out of their schedule to resupply something unreasonable. These people are adults paying a discounted rate vs booking a hotel and I suppose sometimes they need a little reminding. Just be clear to set these expectations in your listing and during the booking process so they are not entitiled. As a host, don't work harder, work smarter 🙂
Whatever items that are non-perishables that you can just buy in stock with coupons, do so. Since you are managing multiple properties, maybe you can have a dedicated trunk space in your car or a large basket with some of these essential items to grab with you during your turnovers. You could also just keep extras stored at the properties locked away and when you are turning over just note what you need to resupply. If you are always keeping extra stock, then you are never running out or needing to run to the store last minute. I don't see the need for a system or software like you mentioned but then again maybe you I am not feeling it to be a burden how you are. Maybe you can keep track in excel and see if there's a trend per x days and anticipate how much supplies you need for a given reservation.
For long term tenants, just state that you only supply enough of toliet paper, paper towels, etc for the first week or two weeks.
As for perishables like coffee creamer, maybe consider switching to the powder kind as it's more manageable to buy ahead of time or just don't have it at all. Yes the regular creamer is better but I mean come on, it's a luxury provided and you can't really expect it. I've stayed as a guest at Airbnbs where they only provided k-cups and sugar and if I was dying for creamer, I just acted like an adult and went to the store like anyone else would.
For laundry detergent just buy those detergent tide pods and state you only are supplying enough for x amount of washes or days. I don't allow guest to use laundry at my airbnb but I suppose if someone were staying one weekend/week then I would provide 1 pod which enough for one wash and if someone where staying two weeks or longer than I would provide that accordingly. This also ensures guests are not over using your laundry machines and driving up your utility bill. I suppose they could always just go buy more detergent and still overuse your laundry machines but hey if they can do that, they can go buy more toliet paper and creamer as well 😉
Good luck!