I have a strange situation with my condo so stick with me here.
Our condo (unit 2) is in a 2-unit building. The HOA does not restrict long term rentals. Unit 2 (zones as a single unit) happens to be split into to smaller apartments (2nd and 3rd floor) with individual entrances and exits, separate kitchens, bathrooms, etc. This was done before we bought it and by looking at the permit history was approved because the front stairwell is technically inside of unit 2, which makes the two floors contiguous. It's like a condo with an in-law unit. Furthermore, we wouldn't have been able to get a mortgage on the place if things weren't above board.
We currently live here and rent out the upstairs apartment to my family, so no issues at the moment.
We are moving soon and would like to keep this condo and rent the two floors to separate parties. It's like renting a room but a whole floor instead. Each floor would have their own lease. My downstairs neighbor (unit 1) made an off-the-cuff remark a while ago, stating that we wouldn't be able to rent out the upstairs apartment if they weren't my family. This has caused me to look into the matter further (incl. lawyers) with little success.
Has anyone ever come across this situation? If so, your insights are appreciated.
Have you asked the HOA about your ability to rent the place as both a single rental and as two rentals? The HOA may have rules about subleasing or leasing to unrelated parties.
Many people look at the CCRs and if they don't see something, they assume it is OK. They forget all about the R&Rs that can contain many restrictions.