Highlighting the strong profit potential and taking measures to address any concerns about costs, scope, or holding risks will make this an even stronger pitch.

I know I need to hold the security deposit in an escrow account.  

I am only buy and hold and am up to 32 houses.

We have an LLC that holds real estate but have run into issues refinancing through the LLC when family is renting or ultimately living in the property so I’m also not sure if this should go through the LLC or be a personal purchase?

Your holding people accountable is paying off.  

Maybe begin with a simple buy-and-hold single family home or do a house-hack.

If not, then a reverse exchange for us to simply hold the property for up to 180 days is possible.  

I've largely stayed away from the "sub-to" buz word, but I have done a couple sub-to flips knowing that I only needed to hold onto them a couple months and I was prepared to pay off the notes if they were called.Sub-to for long-term hold on the other hand has me nervous. 

I simply went to Wells Fargo (Wachovia at the time) and asked for a trust account so I could hold deposits.

Most lenders want to see homeownership and experience with flipping and or holding properties.