Real estate investing is a team sport and at different points in the game different players will play more important roles.

That’s where details come into play.

In a way it sounds easier to me than investing in my business, because I've struggled scaling my business with paid ads (which is the main investment I could make on it) and because with real estate as long as I don't try to play smart (by buying a foreclosure or a fixer or something inherently risky) and if I keep it long enough, then chances are that it would make money in the long run.. don't you think?

The problem comes into play when those milestones are not good indicators of one’s progress towards a goal.

Use surveys to gather feedback on their experience.When tenants feel valued and respected, they’re more likely to take care of the property and renew their leases, saving owners time and money.Fairness with VendorsVendors play a crucial role in maintaining properties, and treating them fairly ensures they remain reliable partners.

How about realizing that when you use the current property taxes of a property you are buying to calculate your per door profit that the following year your taxes will reset to what YOU paid for the property and will likely significantly increase your tax expense - which can take you from a positive cash flow to a negative cash flow on a low cash flow property… now you are paying your tenants to live in the property every month out of your W2 income  hoping for an appreciation play until rents hopefully increase.I could go on and on.  

These are set it an forget it plays. 7.

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. 

If your deal works at an ARV of 300k let's say, and the ARV comes in 250k then if you can't get the ARV lifted via dispute then your deal is dead and you are out the 700 for the appraisal. 

I’ve seen situations like this before, and keeping control of the contracts has always been the better play.