It seems like a similar model for single family HML would be too cumbersome to be worthwhile.

You won't see much difference even if you have stellar credit you won't find much to make it worthwhile the closing costs. 

The end hope is to help all the students create their own businesses that allow them to charge what they feel they are worth, while also doing something that is personally fulfilling.

@Craig Sloan probably they will but how much to make it worth while?

I know this isn't a cash flowing property, but we are in NYC and there has already been an 80,000k appreciation on it...we are sort of hoping that long term the appreciation would make this worthwhile.

There's not enough equity to be worthwhile in a lawsuit.If you get sued, the LLC will protect you from losing your personal assets, but ultimately you would still lose the house within the LLC if you lost the case.With an umbrella policy if you lose the lawsuit, you keep the house and the insurance simply pays up. 

I'm curious if someone else has had experience finding deals this way and if it's a worthwhile endeavor.

David Greene's "Long-Distance Real Estate Investing" might be a worthwhile read regarding your comment about moving around every couple years.If you do join the Air Force, there are a couple platforms that focus specifically on military investors to include @David Pere's From Military to Millionaire as well as Active Duty Passive Income (both have podcasts).I've personally been in the military for about 19 years and currently stationed in England.

Obviously, your specific facts and circumstances may differ, so it may be worthwhile to consult with a real-estate-savvy tax professional to better understand your options.

Sounds like it's not a worthwhile option for me.