Assuming you are using the "cash" method as a majority of 1040 folks do for businesses, property tax is deductible in the year that it's actually paid.

Do you actually do the remodeling yourself, or the designs, etc.?

It's a budget friendly option to some of the other services, and they have engineers on staff + audit defense, but the more expensive cost seg companies ($1500-2500) will actually do walkthroughs of your property via Facetime to more granularly estimate components of your structure. 

There are good cash flowing properties with 30% down without the headaches of actually investing in CA.

Try it next time, you might be surprised at how much $$ you actually save. 

I suspect you are aware of San Diego’s appreciation being great but suspect you have not actually run numbers to determine how much it can impact your wealth.  

Yes, I was actually thinking of looking into the SBA loan options.

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.

Setting this up is only one piece.

Maybe the "classification" isn't the important piece - but can I write off expenses if I occupy a property more than 14 days?