Dan, your first thought, consulting an attorney, is the right approach. 

Good ROI/IRR with long-term appreciation approach.

In short, the trust would be looking at approaching $400k in capital gains taxes.One of my big questions is - when my mother in law dies, does the trust receive a step up in basis on the properties? 

We want to find and understand all the potential creative financing strategies and how they can be used in an LLC.So far I’ve come to the conclusion that private lending or commercial real estate lending may be the only approach that is viable for a multimeter LLC.Some questions I have is:- What is the strategy?

Seems like these companies take the approach of wanting to get your sale once as opposed to having a product that lasts and having a customer for life. 

Follow the Papa Dave Ramsey approach and pay off your current property as fast as possible.

Has anyone had success taking this approach (mixing rentals of 30+ days with typical STRs)?

More of a sniper approach vs shotgun.

Does anyone have a good way to approach a situation like this? 

I am a notary public who is ready to go direct with placing my business with title and escrow companies, I want to know what will be the best way to approach to receive business