You can't do a four month trip with family without a few errors.
Always double check the dates of non-refundable bookings. Not once but twice did we get the day or month wrong on hotel bookings. The first time was via QF Hotels and both they and the hotel said "tough luck, absolutely nothing we can do. That was for a one-night booking. The second time was via Expedia for 5 nights in Munich. They contacted the hotel who were happy to cancel the booking which allowed Expedia to refund in full.
The biggest/most expensive mistake was failing to collect a hire car within 59 minutes of the pick-up time. After that, you are considered a no-show and the booking is cancelled. Sure it is actually stated as such in the T&C but who actually reads the fine print on such matters. And in Australia I regularly show up many hours after the booking time without notice and have never been told of anything like a cut off. My understanding was/is that as long you showed up on the day after the pick time then that's fine. I've also been given cars when I've shown up early.
Being a third party aggregator rental (Rentalcars.com) and with Italy being what it is in July, the hire car company (OK Mobile) at FMO took great delight in allowing me to "upgrade" my booking from a Renault Kadjar to a "much more luxury" VW T-Roc for just EUR400 more. I talked them down to 350 after about an hour. We'd only paid AUD$750 for the 12 day booking in the first place. I've never been so angry, but neither have I ever been subject to such irrational pedantry, and judging by the other counters, making the customers mad as hell seemed to be part of the business model. It is worth noting that we did not pick up our two-month hire car from Thrifty in the US within the cut-off time either and even though it was also through rentalcars.com there was not a single peep about any time cut-off.
Ah well, we live and learn. Just like the guy that checked over the car when we returned it needs to learn to be more observant. There were some decent scrapes on the front bumper that were not there when we picked it up that we genuinely do not know how they happened. We did get stuck in some tiny narrow streets but, and I'm being absolutely honest here, we didn't think we hit anything. We actually celebrated getting out of that close shave unscathed. It's more likely that another car bumped ours at some point but we couldn't pin-point when that might have been. Anyway, they didn't seem to notice or subsequently care and we feel like we've dodged a bullet. We'll call it even.
Just on that, the Amex insurance policy says that we'd need to get a police report to accompany any claim. But report of what? We didn't know anything about it (where, when, who etc). And which type of police - Polizia? Carabinieri? Some traffic looking ones? Can't imagine how difficult it would be for non-Italian speaker (of which I'm one). It was hard enough understanding that a roadside cop wanted to see my International Drivers License during a stop for some reason - "documento"
. Just kept giving him things until he was happy - passport, AUS licence, rental agreement, insurance paper, rego (?). I thought that must be why those were in the glove box.