So I'm thinking about moving back into my rental property instead of renting another place so that I can move back to Portland and hopefully start a new career.My question: How long do I need to rent out my property after these upgrades and other maintenance work to be able to take them as a deduction on my taxes before I can move in for 6-12 months?  

@Kyle Leinhart, @Brent Coombs, yup, if you get the right type of insurance (a high deductible, named perils fire policy) you can get insurance for that amount (quote in hand) in this area.For clarification, I meant maintenance/repairs would be 2% of the property value ($980), not 2% of rent ($264).

I asked if it can be addressed on Tues, the tenant threat me that she/he will get their own plumber and deduct from my rent.

Judgments are renewable and you can do things like levy their bank accounts to get the money back (plus interest and legal fees too, I think) if you do it right.

In general the IRS does not allow married couples to deduct home mortgage interest on loan balances above $1,000,000 ($500,000 for single).  

However, I show VERY low taxable income due to business expenses and deductions.  

This income will be added to your regualar w2 or business income to determine your total debt to income ratio (DTI) against your debts and monthly mortgage costs.To calculate your net rental income, your total rents collected for the year are added to deductible expenses (taxes,insurance, interest, depreciation).

The PMI wouldn't bother me too much as I understand it can be tax deductible from the little research I've done.

There are 2 different issues here:-Deductions from the security deposit need to be made within the timeline outlined by your state. 

If the ORS ever audits you you won't be able to deduct any expenses done from your personal account.