Advice for a novice Oakland real estate investor?

[Jannah M.]

Hi everyone!  I'm new here to the Bigger Pockets forum.  (In fact, this is my first post!)  I'm really interested to see what expert advice I can obtain from the many real estate investors here.

I have been fortunate in my purchase of Oakland real estate over the last ten years.  In 2009, I bought a house in Maxwell Park with an ex for about $250k and we sold it for $520k in 2016.  

In 2013, I bought a condo near downtown Oakland for $320k and have had tenants in that property who have pretty much been covering the mortgage and other expenses.  If I sold that condo now, I could probably get $575-$600k for it.  

And then in 2016, I bought the house I live in now for $648k and plan to sell it in the fall for around $875k, hopefully more with improvements I've made.  

After I sell the house, I plan to do a deferred mortgage on a house my boyfriend plans to buy in cash.  My mortgage broker tells me that so long as my half of house costs no more than $600k, I don't have to bring cash to the table.  This is appealing to me since borrowing more money now while interest rates are low makes sense to me.

Here are my questions: 

What should I do with the condo and the proceeds from my house sale?  

My tenants at the condo just told me they are likely moving out of the condo.  If I don't do a 1031 exchange, then I'll suffer a tax hit on the mandatory depreciation for the years it was a rental.  Tax free, I could walk away with nearly $300k from the condo sale I managed to do a 1031.  If I keep it, then it can probably continue to appreciate both short term and long term, since it's a short walk to downtown Oakland, which is only increasing in value.  Plus, I'd forever benefit from the lower property tax basis based on my $320k purchase price.  I could start to cash flow positive with the next round of tenants, but only minimally.  Or should I go through the headache of the 1031 exchange?  

And, what about the proceeds from my house sale?  I could foreseeably walk away after a sale with around $350k.  I am considering investing in emerging areas of Sacramento that are downtown convenient but haven't arrived yet or an airbnb rental near Yosemite with a friend/ friends or a rental or two in Nashville where my brother lives, which seems to have good rental prices compared to purchase prices.  

Clearly, I am all over the map and would love to hear your thoughts.