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. 

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.

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

Get actual taxes off tax accessors website, get rent toll from agent or owner, get insurance quote from agent, get mechanicals and interior condition from agent or owner (confirmed with inspection later).  

The Tenants agree not to permit any deterioration or destruction to occur while they are occupying the property. 19.ALTERATIONS:Tenant shall make no alterations, decorations, additions, or improvements in or to the premises without Landlords’ prior written consent, and then only by contractors or mechanics, or other approved by Landlord.