This market has effectively collapsed over the previous 12 to 18 months... price for fixerupper properties have dropped to lows not seen in a generation"I still have the property associated with that appraisal.

I work in Healthcare and my goal is to learn as much as I can about real estate investments and eventually generate enough passive income from real estate to quit my day job.

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Can I ask how much cash flow you expect to generate on the property?

I’m considering writing, either jointly or solely, an eBook to help generate leads for RE clients — I’m a licensed CA broker. 

If done properly, short-term rentals can offset directly against ordinary (W2, active) income without the real estate professional status.Losses generated by increasing depreciation with a cost segregation study, can be used to offset active business income without qualifying as a real estate professional.

Here’s a thought… I am thinking about departing my W2 and setting up a separate self employed real estate business and a self directed ira.

If your employment involves being in a physical location, that's the area where a FHA loan can fit. 

The result is the max mortgage payment, with 20% DP (not higher), you can make and still generate the needed cash flow in that micro-market.Don't make the mistake of increasing the DP to get the needed CF. 

I would like to pull some of the equity, give him some money, make some updates and start generating some income maybe with Airbnb or rental.