I am thinking of doing a cash out refi on the rental to fully payoff my primary residence if it would be advantageous from a tax perspective (given the new tax law's higher standard deduction for schedule A, I may not qualify for itemized for W2 income).  

Hi Jordan,It depends on what area you are specifically looking for help or advice on but the general term here from my perspective is risk assessment and aversion.

I know not all of my deals will be successful so it’s good to see someone with the long term attitude and perspective that i know I’ll need in order to be successful in this business.

Your post reminded me of a very similar situation my husband and I had with our first home we purchased together that I wanted to share in hopes to give you some perspective .

So many good perspectives.

Regarding the 3rd bedroom, my guess is that that's having a significant impact on the value from the appraiser's perspective.

No problems here at all.But from the 1031 perspective.1.

With home prices hitting all time highs, I was wondering what experienced real estate professionals' perspective on the Silicon Valley market was?

seems high from JUST closing cost perspective on buyer or seller side (escrow+attorney+survey+prorated tax+ doc)... but again it could be very low depending on how the closing cost is being constructed (may be point or cost from both side etc) ..if you can give a breakout /pic of the closing statement then i can help 

That saves you an additional $600/month you would've had to pay to rent a similar unit from someone else, and the property still appreciates, the mortgage still gets mostly paid down by other tenants, and when you finally move out the property WILL cashflow now that you're getting the maximum gross rents by renting all the units.The deals you're looking at are working, you just need to change your perspective, that's all :-)