It can be done, but don't assume "they will cash flow nicely".

These are all assuming there’s a problem with the current rental or the new properties are amazing.

Let's assume both units would rent for the same price if you didn't live there.

SF and 2-4 MF assume?

There’s a lot of misinformation out there, particularly around VA loan assumptions—one common misconception is that you have to be a veteran to assume a VA loan, which isn’t true!

So when I started getting more inquiries on VRBO, I assumed (incorrectly) this was a similar feature until a few days ago.

There’s a good chance that if lender finds out of property transfer via title records, insurance policy beneficiary, bank account submitting mortgage payments, they’ll assume that John  Smith formed a trust to own title and will not flag the  file for any action.  

The ADU I am thinking of adding is on a triplex property and my understanding on the valuation of these types of properties is cap rates (4-5% depending on the neighborhood in LA) and thus adding more income to the property increases the value of the property assuming the cap rates hold Triplexes and quads are not appraised on cap rates if using conventional financing.  

I assume that when you say "I made no profit" you mean you did not have any deals.

Software automates what you already know (hopefully) - for some folks they get in trouble because they assume the software "knows" and they don't bother to learn it.