I would like to hear everyone’s mistakes, flops, failures.

What you want to consider is if he is able to sue you for damage to his property from failure to maintain your rental unit.I believe, even if the tenant never responds, you still have to formally evict him/her.

If it was a traditional bank then maybe they would be more open to discussion if you were to leave a large amount of your safety net sitting in an account at their bank for a certain time as a "hedge" against your possible failure while also giving them room to lend more to others (because of the $ they have on deposit)? 

Without the tenant’s consent the City must obtain an inspection warrant.California Civil Code §1954 does not apply to the Hayward ordinance because the ordinance affects only the conduct of the City and not that of the landlords.A landlord is required to make only a “good faith” effort to obtain a tenant’s consent to facilitate a City inspection.A landlord cannot be held liable for a tenant’s failure to consent to an inspection of the unit.---------------------- endsnip --------------------Really, the inspection program hasn't been THAT big a deal. 

Having vaguely defined and loosely enforced rules is a recipe for failure.

Meeting him for lunch today and will update my failure again as I learn where I went wrong...:)  If you want to learn some lessons, negotiate with old coverall-wearing landlords!

I think one reason why people actually don't pull the trigger and take action is their fear of failure.

You can still take the expense; however, the penalties for failure to issue are severe.https://www.irs.gov/government-entities/federal-st...I would recommend doing it after the fact.

If I had successes or failures, people could learn from it and really see if this is the life they wanted. 

Wholesaling, having low barriers to entry, seems easy but setting up and following through has about a 99% failure rate.