I have seen similar in some suburbs such as Waukegan, there apartment rentals are going for the price entire single family rentals went at few years ago.

Great question....my answer is total guess vs expert response, but I don't think you probably gain much if anything by doing a cost seg on a single family house with long term renter. 

For those that had SFRs and sold to buy a multi-family, when did you feel it was the right time to scale?

Hello everyone,I already setup a new LLC for several properties that was rented as our family investment property.

Any input appreciated: best areas (Silver Springs Shores/Belleview, etc) for renting to a family?

A landlord does not need to provide a reasonable accommodation for an emotional support animal when:The property is an owner-occupied building with four or fewer unitsThe property is a single-family home sold or rented by the owner without the use of an agentThe emotional support animal poses a risk to the health or safety of other people, or a risk of substantial damage to property (but this risk must be specific to the animal and cannot be based solely on assumptions about the animal’s breed)"Definitely have a chat with a local attorney to ensure your local laws apply, nonetheless since its an owner occupant, it sounds like you have some recourse to deny this request. 

That distinction is important for one very important reason, the asset decisions are being made by the owners (or a direct family member) which eliminates a layer of defense for all these decisions.

I am moving out of my 3.5 year old single-family home as it is becoming a rental next week.

She is a family friend who also has good working relationship with my agent.

My wife and I currently own a single family 3/2, .25 acre lot in Fort Lauderdale.