What's your plan for the first target?

The plan is to create an LLC per investment property we purchase, held in the holding company. 

Also, if you haven't completed your estate planning yet, if you own real property, now may be a good time to consider that for your family. 

I'm planning to reach out to see if people are interested in investing equity in a condo to get it at a discount, maybe at construction cost. 

My plan is to 1031 this into a duplex.

(I’m working on getting the wife onboard with our long term plan, too.

You get grandfathered into the codes that were in place at the time, you get the old setbacks, you don't pay an architect, engineer, city and permit fees, plan check costs, school fees and other costs that will not come with an existing house.Not saying that you can't build new for less than a remodel, but not usually when you add in all the costs above. 

I'm planning to use VAs to help with the first part that you mentioned - qualifying homeowners based on interest in / willingness to sell.

Looks like one is better for a flip and the other has an incredible upside with equity so we plan on holding that one. 

@J Shoe A trust isn’t used for asset protection purposes, it is purely for estate planning.