Maximizing W2 Tax Deductions - Quit second job or keep working 2 jobs or STR?

[Angelo Cortez]

I have two W2 jobs. W2 income is total ~300k/year. I already co-owning a duplex, but the VA loan is under my friend's name, so I don't think I can quite deduct that yet; I have helped with furnishing / renovating one side of it for an MTR, which has taken ~15 hours/week. We are planning on converting it into an investment property next year since that's the earliest we could do it.

That said, I'm debating on what to do as my "first"  real estate investment to maximize my yearly W2 tax deductions. Have around 90k cash and 90k in stock. Possible strategies:

1. Quit 1 job, get 1-2  investment properties in Sacramento, cost-seg them, and attempt to claim REPS (may be too late for this year as I just started halfway)? .

2. Keep working 2 jobs, get STR in San Diego, cost-seg it, and use STR loophole.

3. Quit 1 job, get STR in San Diego, cost-seg it, and use STR loophole.

[Jeff Nash]

@Michael Plaks gave great advice.  

It's been mentioned a time or two on here, but another option you don't list and that may be helpful for higher earning W-2 folks (or accredited investors) is to invest in oil and gas.  There is accelerated write-off for intangible drilling costs (IDC), lease and well equipment and percentage depletion.  It is a good choice from a tax perspective, but from an investment standpoint you have to do due diligence, more so than with other types of investments.  I'm an advocate of it in the right situation, with consideration given to someone's risk tolerance, investment objective, time horizon, etc.