No question is too silly, trust me, I’ve asked them all.

This means you need to pad your rehab costs, make sure you have trusted service providers that do great work, and when you run comps be sure to bring them down a bit and see if the deal still makes sense. 

With mutual trust, your agent will be able to put more time and care into your searches, evaluating properties for you, and not having to worry if their time will all be for not.

In order to have checkbook control, the IRA account will need to be at a trust company that will allow the IRA to invest in an LLC (where you will be the manager and your IRA will be member - an as manager you will have checkbook access to the LLC bank account).

It seemed overkill to me but I'm not sure I can fully trust my instincts yet.  

1099, social security, trust payments, annuities, etc?

Talk to a tax advisor that you trust or know someone personally that has high trust with them.  

As always, I trust you in all advise!!

The national organizations can have a lot of money backing them from Alumni and it would be a very long term lease. 

The drawback is you need to build trust and relationships upfront.Both have their place, but private money tends to offer more flexibility, while hard money is more structured and accessible if you lack personal connections.