It is always good to start a relationship with a lender / Mortgage Broker prior to identifying a property as they can give you some great guidance on many of your questions and help you solidify your plan of action.  

I'm not a lawyer but even for a small job you'll need to have the parties identified, the scope of work, the draw schedule (when and how much you will pay the contractor) and any other conditions that are appropriate.  

My main goal is to identify a good handyman, ready to go Day 1, so I’m not struggling last minute when an issues arise.

I am new to wholesaling and I have identified RVM as probably the best way for me to get started while working a 9-5.I have chosen to go with slybroadcast using callrail for now, I am open to suggestions on other systems.

There is a lot of work you have to do as an investor in identifying your goals, your needs and reasons for wanting to invest in real estate, identifying whether or not you can truly be a passive investor, etc.  

But don’t now how to identify the value of the property.

You could try to identify ways to make up for that lost cash flow by doing something that is within your core competency. 

With lots of practice you will be able to identify a good deal quickly and jump on it when the opportunity presents itself.

The type of self-directed IRA that will best suit your situation and goals will drive the process of identifying the right firm to work with.A self-directed IRA custodian is a processing entity. 

Identifying exactly the type of asset protections you are hoping to achieve will help them answer your questions.