We're comfortable with that though as we want assurances that their financials are healthy.

You've already put in some great thought, and with that ADU, you've got a lot of options.One thing to consider is starting with long-term tenants in the ADU for a bit and then transitioning it to a mid-term rental (MTR) down the line when you feel more comfortable.

This enables you to get your feet wet while seeing how the experience goes and once you get that settled in and you're comfortable with your processes then I'd start branching out into other investments whether it be local to you or out of state. 

I always go in with a simple offer of this is the rent, and we are also comfortable giving you a (insert something you need to do anyways like a basic, white paint job or a new appliance).This is one of the most uncomfortable parts of the business though, and the quicker you get over being able to have these conversations, the quicker you will be successful in this business.

I agree, with Joe, it does come down to you and how comfortable you are with house hacking and if it makes sense for you financially and for your family.

I feel like the more people share, first hand experience in this space gives folks confidence and one of many reasons it doesn't feel comfortable to me.

I’ve designed and built a house to sell, I bought and flipped a foreclosure, and currently in a live in flip.

Make sure you’re comfortable with that risk.If your primary goal is tax benefits, transferring the property may not be necessary.

Look for the Certified Cost Segregation Professional (CCSP) designation, which means they’re certified by the American Society of Cost Segregation Professionals.

I am in the works of creating systematized courses for VAs designed to make the onboarding process easier for when I bring them onto my team.