If i may, let me expand / detail some of your thoughts with my perspective.There should a separation between a "real estate business" and "real estate investment." 

I suppose if you are that good in sales and have a market to get $1mil transactions, sure...You have to separate truth from reality...

Do you run each property separately in individual LLCs/bank accounts?

3 separate residential mortgages How did you add value to the deal?

On a separate note, if you are worried about not being available to sign docs while you are away, you can resolve this conflict a couple of different ways. 

If they are two separate properties, you can’t use fha fir both, as you can’t owner occupy two properties.

It’s currently a 3/2 w/ an half finished basement potential 1/1 with separate kitchen and driveway.

Now, I never ever go to one of my properties with the exception of when my wife forces me to see the vegetable gardens she works on almost every day.By not going to my apartments I have no personal contact with my tenants and this allows me to keep emotions out of my decisions when a tenant pays their rent late.

Happy to provide more info about myself, but will cut right to the chase:In today’s market, if you see a property listed for 4 months with 2 separate pending sales that did not go through, is it safe to say that is a red flag?

@Shahar Joseph  a support dog (probably an emotional support dog) you cannot legally refuse however you can have a policy for documentation of a need by a qualified professional and you cannot charge for and ESA.