I stumbled on some information about short term rental tax benefits as it pertains to lowering W-2 Income. 

But considering all the expenses (PM, leasing fees, cap reserve, maintenance, taxes, etc), it has been showing as negative cash flow. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

My biggest surprise in trying to fix this is that the administration fees went from approximately 10% to 30% on my revised quotes.  

What I mean by this is considering how much your down payment returns to your net worth (appreciation, loan paydown, tax benefits, AND rent avoidance).

One thing to consider when you are budgeting is the taxes and insurance.

If it's important to be near the Bay area then maybe consider the Tahoe Reno, NV market because it's only a few hours away if you need to go to the office and it offers a landlord friendly environment, low property taxes, and no state income tax.

My insurance and property taxes are also set up in this manner. 

I use Innago as a management program which allows different taxable entities for the rents, which would assist when it comes tax season.

Look at lists of properties that are on the Sheriff Sale, and Tax Sales, as some of those could have assumable mortgages, and provide a list of potential assumable mortgages, where the owners are potentially losing their properties.David KrulacBigger Pockets Podcast guest #82