This can work out for you but your risk is in buying the correct property with good mechanicals and modest deferred maintenance. 

We would like to avoid probate, so a land trust can be a good mechanism. 

Everything is on auto pay and rents are paid online.

For instance, I know a few shop owners, mechanics, restaurants, etc. and got permission to put my business cards on the cashier counter.As far as the numbers, if they work and you can see them working in the near future, then why not?

Yes im curious about the mechanics of adding to the HUD.

the lady I talked to said it counts against you when you do something like going from an IT professional to say something like auto mechanic because you're changing fields.

I might just have them do foundation/framing/mechanicals/etc... and I'll finish it off with drywall, paint, tile, cabinets, etc...

Its a very sophisticated structure, so just make sure you know and understand the mechanics of it.

Now I’m working as a project manager at one of the world’s largest auto manufacturers.

Paint every surface that can't be cleaned enough to look acceptable and ensure all the mechanicals are working properly.