After the last crash, it took ten years just to recover the losses.

can you share the math that indicates that loss?

In addition, if you are not a real estate professional, you might be taking additional losses in your real estate that you can't deduct. 

I think I’m dealing with a management company, is there a chance they would like to off load this property before year end even at a loss to avoid paying taxes and such? 

Why do you want to start at a loss, and lose even more money exponentially starting from the day you close?

I'm pretty sure you're onto something.I know that with a typical rental property, you can carry losses forward into the next year.

Don't do it unless you are either willing to eat a loss - perhaps significant - or are OK with ending the friendship. 

The fact is, he will have trouble saving up for 2 down payments within the next year, so if we invest in a property together, it would be ideal he live in the property for his sake.I've suggested that he should pay the full rent in the form of owner contributions (or some other way to not get double taxed on his dollars) to an LLC we would own (we're intending to buy a 6+ unit property) to make up for the loss of income by him occupying the unit.

I don't see me splitting my commission as a loss, you gotta pay to play and experience is worth the price.

The idea is that the BRRRR properties would generate a paper loss yearly (with depreciation, etc.), would I be able to use the "loss" to offset any profit I make from a fix and flip in the same year?