Now, lose the fear, loosen the shackles, and turn off the machines. 

@Michael RayYou are getting a lot of advice to sell from people who likely don't have investments in the Bay Area or other high cost investment areas.First off - if you sell the property - you will likely lose 6%-8% right off the bat through seller commissions and other seller related costs.You would have to buy another property at 6-8% below market just to make up for it right away.Second, you have to determine what the property is appreciating at on an annual basis, while you are not cash-flowing, the value of your asset may be appreciating at a higher level than other asset classes.As much as people are saying they are leaving the bay area, there is little area's around the world with great weather and atmosphere(minus the homelessness issue) as the Bay Area.Cash flow is good as it brings in income but asset appreciation is where true wealth is created.

Yes it is common, but it's a load of *** that they didn't disclose it.We lose potential clients all the time who fall for competitors claiming they don't charge extra for maintenance - but we know they are lying and just hiding it.

The majority of them aren't really motivated, some I lose to competition. 1,000 letters really isn't a high volume even when you're using a targeted list.

You could easily lose lots of money and time with a contractor. 

I did not look out for the special assessment but was purchasing from a wholesaler and did not want to lose out on my down payment.

And what are the tax implications if I make money/if I lose money at the end of the year?

I am moving in this direction myself.I agree 100% with your emphasis on data-driven market selection, standard operating procedures and automation.

I just want to get my feet wet and want to learn and not lose tons of money.  

Always worth the search, so your cash isn't losing value with the banks current sub 1% interest they give you!