If you are a safe driver I would just try to get the biggest deductible you can handle because that will help to reduce the premium you pay.

You can outsource it in the future, but you would be reducing your cashflow by $3240.

This all reduces the risk of losing money to an unethical contractor,  and also allows you to fire a contractor and get a new one a little bit easeir.   

Yes if you refi to a 30 year loan you will have lower payments, but for 19 additional years, and most likely at a higher APR for the longer loan.There are some great ways to use HELOCs and Home equity loans to reduce the amount of interest you pay, aka more money to invest.  

Track everything you are responsible for and review that regularly look at them in an effort to reduce expenses and possibly increase your income.In the begining, just do what is average for that subject neighberhood.  

The idiots at the county think they have done us a favor by reducing the overall tax rate a few mil then the appraisal district jacks up the values.

I am selling a property to a buy and hold investor and accepted a reduced price for a "time is of the essence" quick closing.

You are reducing your taxable income by $119 per month.

As such, again they will beat out a pre investor 100% of the time and for what they are doing (basically locking in a place to live at a reduced rate) its rational.

Look into CPA's that are able to reduce costs by working virtually with you.