What we're struggling to understand is how to underwrite/estimate the paper losses that a MF would produce and IF this strategy is worth it from an income/tax savings perspective.

Old school ledgers and rent rolls written on notebook paper...

One idea I have is to "shadow" a real estate investor (although I am not entirely sure how to go about asking for / finding this kind of opportunity), but I am wondering if anyone has insight into other ways to gain a comparable level of experience.Experience on paper you can't get until you go through a project on your own or have a big enough piece of. 

It can be quite intriguing and interesting to hear of many of these returns and great on paper assessments, but the reality is, they rarley pan out in real life. 

Those are the neighborhoods that cash flow on paper, but don't in reality.  

I find newer investors over-using acronyms when they don't even know they mean - ROI, COC, BRRRR, etc.The most glaring old school vs. new school knowledge term that I think people should look to hear, not say, is holding paper.

During the mortgage crisis i worked as a loan officer for a very short period , in that time frame i saw how shady that part of the business was, customers where signing documents blind and for that very reason most lost their homes, everyone was taking full advantage of the situation and trying to get a wealthy as fast as possible before the party was over.What i dont like working with loan brokers/officers is that there is a lot of jargon in their paper work that they only understand , i wouldnt want to get stuck in bad mortgage deal .

After operating 1 rental for 2 years and another for just a few months, I just got notification from the code enforcement at my municipality (whom I had visited in person) that I didn't file a paper correctly and fines are possible.

The last time I went through tenant applications it was a paper/pencil situation.

***You'd want to make it worthwhile to foreclose and also be safe***If someone is an A Paper borrower just needing to close fast, some of my investors will go 75 LTV.You can also always feel more comfortable on a purchase rather than a refi, as people are bringing skin into the game, not trying to exit.