Originally Posted by AutoSlash

Just one minor point... Consecutive rentals or rentals with a duration greater than say 30 days that the rental company decides should be broken up into separate contracts may be considered as a single rental and denied coverage from the insurance company. There's been lots of debate about this on FT in the past, and we don't know if there ever has been any case law to settle the matter definitively, but it could be a risk.

Generally, if your policy only covers a rental of X days, it's recommended to have a 1-day gap in-between rentals with the same company or to switch companies before you exceed the max rental length to be on the safe side. Then again, it may be no issue at all, but it's worth mentioning given the risk of a denied claim.