But you don't lose any money having money in TSP and your ROTH, assuming they are both investing in the S&P. 

If you can utilize owner occupant financing and force a decent amount of equity at the same time, it's tough to lose on a deal like that, especially as a buy and hold. 

My current tenant who is on a month to month lease gave me notice on May 1st at around 8:00 PM that he will be vacating his apartment end of month due to a job change.He had the capacity to give me ample notice at least a week earlier than that and it would have given me enough time to find another tenant for June as I am seeing  Prospecive tenants also need to give one month notice before moving to their current landlords,so I will end up losing rent for June.Did my tenant technically break his lease by not informing me by 11:59 pm the previous day?

No matter what the cause, you can't lose that kind of money and survive... 

This is how you lose that illegal unit by them reporting you.

If they don’t buy in two years they lose there option money.  

Factors for this are they are passive and notes are typically considered ordinary income so better tax advantageWhen buying property you have to be careful of leverage and UBIT as well as you lose the tax benefits associated with it as well since it’s already tax deferred.

It sounds a little strange but they actually lose money on loans this size.  

My choices are to either roll it all back into my 401k and wind up the c-corp, or invest the funds into real estate (short or long term rentals or maybe crowdfunding some other type of asset class), roll the dice with another online venture (which is my wheelhouse but after losing a bunch of money this last time Im hesitant), or something else like stocks or bonds.

Put alot of bids in would lose them to cash buyers.