Most agencies are slow to process paperwork, have a lot of bureaucratic red tape, and it is difficult to get them to respond to inquiries.

Prior to the GFC I had a pretty robust HML company with 20 plus employees doing 60 HML a month through out the mid west Rust belt and deep south by 2010 It was over like 95% of all HML we all got our butts handed to us..

Qualify the contractor and highlight the benefits of working together which would include consistent work for them and regular paycheck.Personally, I'd buy the materials and never pay any money upfront, a "red flag" on its own.

Smoking cigarettes is also quite legal, and also prohibited under the lease.I think your argument on unit count is a red herring here. 

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

Yes, the contractors were bad people, but there were hundreds of red flags waving in your face and you ignored them all. 

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

I think most hosts give 5 stars unless there is a serious issue so even a 4 star is a red flag for me that I would check into. 

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. 

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.