@Kieran Collings - I'm an investor, flipper, and own and run a local property management company.  

Quick Question to the group:lets say you have a LLC which owns properties - call it Property LLC. 

Has anyone found a property manager in south Florida (that covers Fort Lauderdale) that they really like? 

Anyone have any experience with placing a flat billboard on the side of a building in Philadelphia? If so, can you send me DM. Thank you

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

I can handle about 80% of the work for a property flip.

LA City here~How do you market your rental to insurance companies directly for temporary home placement?

@Kevin Hoover, with certain types of entities it is possible to contribute property to and distribute property from that entity without triggering a tax event. 

My accountant told me that I needed to move the property into the LLC (change the title/deed) for the property to be considered a rental. 

I'm a Realtor with a couple properties listed in Boise, ID and a neighboring town for my investor/client that are currently rented as co-living or rent-by-the-room and getting killer income. (7.3% - 9.5% Cap rate) So far, every inquiry has been baffled by the concept of co-living or rent-by-the-room and immediately ask if they're being run as a halfway-house (which they are not).