I've had fantastic luck with purchasing two side-by-side condos and creating a "parent" listing where a single party can rent both sides as a combined unit--usually at a premium to the combined price of the two child listings.
The only issue is that this makes running month-end reporting a little frustrating, as I have to manually adjust numbers (taxes, owner statements, etc.) to account for the revenue of the "parent" listing.
OR already has a mutual blocking feature, but it'd be nice to expand that and have the system be fully aware of parent/child listing relationships (e.g. if a parent listing has two child listings, then revenue can be assigned 50% to one and 50% to the other [or any other customizable percentage and combination of units]) for the purpose of end-of-month reporting and such.
Yep, from a reporting side it can be complex if parent listings are split across owners -- you either have to create a combination owner or do things by hand as you're doing.
We are thinking about how best to address this, but it is pretty complex to get right (what if owner share changes, etc.). And it should also flow into other places like occupancy reports etc. Lots to do!