It surpasses my banker, whose last name is Lenderman....

I personally can't imagine going negative cash flow for speculative gains San Jose's appreciation has far surpassed 3% per year.  

After you pay off the student loan debt you can move to a bigger house and you will have a good rental property where by then the rent will easily pay the mortgage and provide you a nice income that will easily surpass tbills, bonds and/or cd's.

You don't think you'll surpass 6 transactions?

My intentions are to build up the safety net again, surpass it, then work on the curb appeal of both houses.

While only as little as 34.2% of homes have been able to surpass the previous peak across the country, the scenario varies widely zip code to zip code and county to county.

When we surpassed the 10-loan limit for fourplexes, we faced getting commercial loans--regardless of the property size.

Maybe $1-2k, nothing that it would take years solid appreciation to surpass.

Once prices surpass the point in the center, your ability to cash-flow disappears (though there are a few exceptions).Again, although there are a few exceptions....Generally... for SFRS with 4 bedroom / 2 baths, once price moves beyond $120/125K, generating cash-flow becomes difficult if not impossible.  

And those same people typically don't take any steps to improve their lives and don't want to see you far surpass them in life.