Nice investment, net loss of $2K/mo not even including cap ex, management, etc.SF Bay Area is very solid and a complete blue chip so it's not going to depreciate pending a crisis but buying with appreciation as the goal (and not just gravy) isn't a good bet.How much better could you do with the $2.5M on a 40 unit apartment building in Florida or Texas? 

Remember, a 401K or IRA may have earnings or losses.

I am concerned about giving her cash you don't get back and then, at the end of all this, you take a loss.  

But the position-sized and stop-loss monitored momentum stocks have the capability of very high short term returns which I want to keep in a tax free account ($1,000 that grows by 1000% would be a hefty tax bill).

Seniors lending $200-1M to bad deals with a total loss have no income or time to recoup the loss.  

Take your core business keep making a bunch of money then slowly build up your outside investments.. fix and flip is a lot of work and more risk than most will admit to .. now of course if your doing it all with cash you don't have bank exposure but just loss of principal exposure.

Make sure you wrote off any 2106 loss on your Schedule A, that it's being removed from your commission income.

From what I hear, many homeowners simply avoid putting in claims as it results in a big increase in their premium and unless there is a loss of a sizable nature, they just eat the costsThanks

There are so many potential mistakes you'll make getting started that the losses will far outweigh the gains.  

At the end of the year when you do your taxes you'll report each member's share of the capital, profits and losses.