You have a lease/option contract signed with the seller and your intentions are to sign another lease option with the buyer and then assign this contract back to the seller.

I'm pretty sure he can find me properties before they hit the MLS and other good deals, with the intention to fix and flip.

No deposit, No deal.This is what homeowners need to demand to keep THEIR property from being tied up by people with no intention of buying it!

I've got rentals and enjoy wholesaling although my intentions are geared towards larger multi units and or mobile home parks in the near future.

There is too much government involvement now.A driver CANNOT buy the amount of insurance they want but has to buy UNLIMITED no fault personal injury insurance.EXAMPLE If someone is trying to commit suicide and purposely drives their car into a tree at 50 miles per hour all of their injuries are paid by their insurance including UNLIMITED pain and suffering and damages.An insurer could be charged $3,000,000.00 or even more for something you intentionally did to yourself.And yes the Detroit mentality makes the Michigan requirement unworkable.

I have a friend who actually bought his first house with the intention of renting out two of the bedrooms.

It's ok to offer less, but....I'm curious what your intent is w/ the property.  

I understand this question is a little vague, but regardless of intent, holding, renting, or appreciation, what period are you most comfortable with buying from and why?

You must have the intent to hold for rental or investment purposes. 

@Patrick BarkerAnother suggestion to bypass the Realtor and keep you from getting preapproved would be to write  a simple letter of intent (LOI)The LOI has been used effectively by people such as Grant Cardone who was featured on podcast #108.A simple google search of this term will show some samples....good luck!