It doesn't make sense be in a -$800 a month (at best) while paying a huge monthly payment with high property taxes.

Hi Emily, I'd say Azibo, Stessa, REIhub are good rental accounting options that offer income/expense tracking, financial reports and tax reports (Schedule E).Azibo and Stessa offer business bank accounts.

We file a joint tax return.I put this question here to see if this is even practical or possible to pursue?

In this case, how and when can we incorporate those expenses into our taxes? 

Just like your saved after- tax money in your bank is not taxed each year. 

Also your cost associated with holding (utilities paid by landlord or tenants, taxes).

California for example taxes, HOA's, Sale prices all seem to eat any cash flow right out of the gate.

No W2, tax returns etc.

You just have to have legitimate self employment activity.  

Is it real that you can save on W2 income taxes if you have a short term rental.