I'm more concerned on if it's going to be a good deal or not.

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. 

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

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.

The money for the mortgage most often comes from a hedge fund type of investor or the Government, the Servicers concern is, is the loan preforming, is there insurance on the property and if the guy on the mortgage not creating any issues?

With the amount of losses you have had it might be a good time to try and offer a Cash for Keys deal for the tenant to move out and just cutting your losses while there is uncertainty about what is going to happen in 2021.

Starting with a mentor is very smart – it really cuts down on the learning curve, especially with something like a fix & flip.

@Lorenzo Wright, Once I've established a relationship with them, I'm not as concerned.

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.