My wife and I file separate because if we filed jointly we would have to pay 10% of our combined taxable income.

It’s just the valuation.If I don’t fight this valuation, I am paying taxes on a higher assessed value than what I bought it for a year ago (they do 5 year assessments) and it’s effectively a 40 percent increase in taxes vs 2017.

Of course the bolder the target, the less likely it is and probably less than .01% of people could pull this off.More realistic advice is to get as high of paying W-2 job as you can, save up, put 5% down on a 2-4 unit, manage the heck out of it, and then leverage that experience to do a larger deal using OPM.

@Maxwell Hinesmakes no sense - you'll be negative and never be able to pay the HELOC draw back with the cash flow you don't have from the house

Pay attention. 

Will someone lend me money to pay off another hard money loan?

I am agnostic on geography other than looking to stay East of the Mississippi and out high tax/high regulation states. 

I try to pay it back once in awhile. 

A good financial planner will save you a lot more in taxes than they charge. 

In CA MF is rent controlled but SF is not rent controlled.  12) the ADU will result in property tax increase more based on cost than actual value added   item #1 implies the property tax you will be charged is more than if it was based on value.My top advice is make sure you know the value added to the property by adding an ADU. good luck