Quote from @Marc Zak: In the market where I live (San Diego), appreciation has been strong and many predict it will continue to appreciate in the long term.However, with current interest rates (6% at best) and property tax (2%), the annual cost burden is 8%.Am I correct in saying that appreciation has to be above 8% annually (plus whatever my maintenance and vacancy costs are) for me to make any money in this scenario if the property is cash flow neutral?

At the very least she will be able to carry forward the losses for a very long time, helping her get into cash flow positive status much faster. 

Purchase price: $2,500 Cash invested: $5,000 Single family House (2 stories), 3 bedrooms, 1 bath. 1100 sq ft. on Corner LotSingle car garage with 16' x 24' lean too.

I also keep a fair amount if cash (10%).

Why not just sell it and get a cheap car, pay cash?

You likely only made a down payment of 3-20% ....but you still get to write it off on the full value across 27.5 years.So 400k/27.5 = 14,000 ish a year of a write off where during the year you didn't need to incur an actual expense, no cash outflow. 

So about a 35% cash on cash return for my buddy each year on his $100,000.

Analyzing an investment with the Cash on Cash return makes more sense to me.

Purchase price: $55,000 Cash invested: $440,000 Currently under construction and pre-leased for $6,195/month, this 7-bedroom, 5-bathroom student rental in Clemson, SC, was built using investor cash and designed for high-end student living.

Super cool idea I think - win-win for everyone, you make extra $, cleaner makes extra $, guest gets what they want and can have a unique memorable experience.Opens the door for lots of different "package" types What's the downside?