Appraised at 250k took 80% paid off my private lender and got all cash back out. 300 a month positive cash flow.

we've been asked the same question by a dozen or so good friends who live in/near SF about whether it's worth postponing the ownership dream, given where the bay area market is in 2018. personally, I think that right now is the time to hold off on entering the bay area market... unless you find a truly off-market, discounted opportunity through networking or a personal connections.sidenote: moving to the east bay (alameda, particularly) actually shortened my commute time into my day job in SF, compared to when i lived in SF. i'm sure you've heard this perspective before, but there's goodness to be found in the east bay, if you are dead set on buying in 2018/2019.from an investing perspective, there are still strong returns to be found outside of california. that's why we recommend to friends with capital that they consider looking into investment. that way they can start building wealth now and position themselves for buying that beautiful home when the time is financially right. sidenote: i recently posted on a similar topic on this thread. you can see if you scroll down and there are dozens of other helpful comments on this topic, on that thread: https://www.biggerpockets.com/forums/12/topics/587593-general-do-you-rent-or-own-the-home-you-currently-live-in?

Sometimes those losses actually put you in a better financial position if no personal harm was done.

I would love to hear some war stories, as any positive feedback, lessons i can gain from others would be truly valuable to my upcoming journey. 

Exist positive cash flow from day 1 is very important to building towards retirement. 

Second, the point of posting a property for rent is to receive inquiries, so if you are not in a position to promptly respond to them and show the home, you may consider hiring a professional management company to do this for you.

This property has positive cash flow and we aren’t urged to sell.

So they're being excessively conservative, in my opinion.As long as your CPA agrees with my position (does not matter which spouse or both own the property) and is willing to defend it before the IRS - you're good. 

Would you let random members of the public go wandering through your home without being accompanied by someone in a position of responsibility?

Just be sure to explain to them the difference (risks vs rewards) of being in lien position and being on title.