To increase your business as an agent I would high recommend the (red book), The Millionaire Real Estate Agent, you must know about it since you are with KW. 

A "flip" can be pretty damn far in the red but still be "viable" if it makes good TV that generates a bunch of add revenue. 

What type of red flags do you see with leasebacks? 

Couldn't disagree with that statement in bold more, at least in my experience.

That is a big red flag to me.

So I’m red lighted until I finish instructor training.

Writing of 2 home offices (or 4 possibly, in your case) would be a huge red flag for the IRS for the benefit of a few dollars in tax savings.

Also, wife asks to move in ASAP, which is a red flag.How do you say no to prospective tenants requesting for showing for a rental property? 

Also, you may get away with that in Red Bank, and being pet free can make sense in an apartment anyway, but in many markets and SFH you cut your own throat with that policy.

Fast forward 3 days later and we still don't have official application or signed lease, but they have sent us an email with extensive questions regarding the lease that have raised the last red flag (including a lot of quotes regarding state laws).