I am not sure really my concerns, i would prefer to lmow them now and evaluate before doimg it then finding out the hard way.

But since one LLC is not the parent of the other (individual stand-alone entities),  we're not sure how to properly account for this transfer. 

You need to look at the individual property to determine what it is worth. 

If you can "pre-qualify" or rather get a terms sheet from one of their preferred lenders then they will bring you deals as they are shopping them around. 

@Kyle Baron  is not difficult to file conciliation court case nor do you need attorney to represent yourself if you own the property as an individual and not in a company.

If so can I be on the deed as an individual and he as an LLC?

Usually you will pay for insurance on individual properties, and yes your liability and fire policy should be much cheaper than a homeowner's policy which is used for people occupying the home.

People don't like change.After doing it a few times now in a B to B- neighborhood, I'd much prefer to inherit an empty house, do whatever upgrades I need to do for the rents that I want to charge and then screen, and place my own tenants.

If we split costs 50/50 for everything, how do we factor that in to our taxes since each individual will have a loan in their name but the costs and profits are split?

I’d prioritize my lifestyle preference over potential appreciation when deciding between those two different environments.