You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

He was knee-deep in a 1035 exchange that felt like trying to translate legalese while juggling chainsaws.

The red flag here for me would be the willingness to overpay when they’re not bidding against anyone.

You’ll often see sales with 100-200% swings within the same area, which makes having deep local knowledge and understanding the nuances absolutely critical.I do this for a living, and even with experience, comping in Detroit can still be challenging.

Designed by Montreal-based Felix & Paul Studios, known for their award-winning VR experiences, this immersive attraction will transport guests on a deep space mission.

If the foundation / footing isn't deep enough, frost could have raised one side of the house and caused cracking.

It’s all about finding a balance between purchase price, financing terms, and smart rental management so you’re not forced into the red.

I just paid my attorney 15k today in just fees for 4 entitlement contract red lines and we arnt even under contract yet!  

I definitely ended up passing on this "deal" based on the red flags.

Also, real builders/experienced developers will often have a true technician, i.e. a civil engineer, architect, real estate attorney et al at least glance at the property info to make sure there are no major red flags.