It's tough to get started but both are great strategies to generate a little more year 1 and 2 cash in a tough market. 

I have heard of people staying long term then cancelling their booking consequently resulting in a blocked calendar and no pay. 

A great investor focused agent, coupled with a great PM, can get returns in a bad market if they know what they are doing.Investors should pick market based on barrier to entry and their available Capital and their strategy. 

Of course, talk to CPA as they said previously. also ask if you could collect rent and put in a money market or something for her as a forced savings. 

We are currently living in a home that my parent's paid for in cash.

Big amount of square footage in a high cost area. 3/3 made it attractive as a starter house.

The idea here is to buy the land, farm it in a cashflow positive manner for some number of years while density increases and eventually sell or develop ourselves. 

50 units from 500 sqft to 2000, on a park in a mid size city in norther ca.

I would love to hear how it goes in a year or so for the investor. 

The unfortunate truth about cheap properties is that a hot water heater and a roof still cost about the same as a proprety in a more expensive areas so your repairs/vacancy/capex is going to eat up a larger % of the gross rent than a more expensive property even though the $ might be similar.