I'd love to move into another fixer upper for two years so we could flip tax free or live in for long enough to use our FHA loan.

You have to pay for their time and expertise and $250 sounds far.

Is taxes going to be higher today or higher in the future? 

My property taxes go up max of 2% a year with Proposition 13 (unless I do a significant renovation causing it to be re-assessed). 

Rules vary significantly, and you need to be aware of licensing, taxes, and any restrictions.Local Market: Analyze the STR market in your target area.

-While rent would be more expensive month by month, the idea of being able to take my equity out of my home and also being able to reduce annual repair costs, property taxes, etc. does seem appealing to me. 

This would allow you to indefinitely defer all of the tax if you sold, and use the tax you would have had to pay, to purchase something nicer in an area with a greater growth potential.   

You have tax benefits through depreciation and you are gaining experience via property management.  

Personal Financial Statement Borrower’s Schedule of Real Estate – or- Resume illustrating experience2-3yrs Personal & Property Tax Returns – All schedulesPrevious Year and YTD Property Profit & Loss statement w/ detailed expensesRent Roll w/ detailed lease informationCopies of all Leases3mo.

Some people use their IRA to fund fix and flip's and keep the profit in them tax free.