The goal is legitimate: due to complex tax rules, you have opportunities to game the system by selling some of your investments and intentionally generating either gains or losses.

You make revenue here and there but the goal is to generate enough in the winter to sustain all the expenses for the entire year. 

Additionally, how are you navigating the refinance stage, with lenders tightening up are you still Able to generate your desired profit by refi? 

Got the lead from the cold calling agency I use.

However, vacancy means covering 100% of the expenses.Multifamily properties almost always generate higher cash flow due to multiple income streams, which also reduces the risk of vacancies.

My wife is a first generation Mexican immigrant and she loves real estate.

Best thing to do is have it I a high yield savings that is generating money on your money and is very liquid when you need it.

This often leads to complacency which is seen by the trail off of attendance at these meetings.

This is relevant for multiple reasons 1) appreciation is where the real wealth is generated in RE 2) real estate has tax advantages over cash flow 3) in CA property tax increase is capped.  

Assuming this is in fact a good deal, and your friend is a qualified GC, instead of trying to be the lead investor, he should be searching for someone who has the balance sheet to take down this deal on their and be a transactional participant.