In my state the standard contract used by realtors addresses this issue by allowing the agent to check a box specifically to limit the seller to keeping the EMD as opposed to going after "liquidated damages" like that.

We plan to rent out the main house and ADU in the future but also concerned on the return if/when we do sell. 

We only address power outages, as such:Landlord is not liable for any interruption or malfunction of service.

Then address the floor...and I would go with the R-30...better to have it compressed just a little bit than not have enough IMO.

True the new owner will have to start his own account, but he should have a built-in revenue stream from repeat guess that will search for that property by address.

You'll want to explore this with your accountant and see what side of the fence they are.What is more a concern to me is your plan to let the property sit for a couple of years and then move in. 

However, we are taking over from a PM to self-manage and are inheriting the current setup.Our biggest concern is that this first communication from the tenant was a sob story asking for $500 back/off rent.

I'm more concerned about appreciation and equity so I'm willing to trade the cash flow for it, but I don't want to be in a situation where I'm barely breaking even and the stress that comes with it.Looking for ideas how I can tap into that equity to grow my portfolio but still getting some kind of cash flow to be able to make the monthly payments1.

Not gonna give address's here because not trying to market them here, just pointing out reality that when your a 24-7 professional "hunter", you tend to know where the deer are all but on demand. 

If you were looking at buying in Florida, but your lender is in NY or California, they dont really have to be as concerned about their reputation because the realtors (most likely) will never work with them again. #1 is the primary reason, but #2 does factor in as well.