If you're willing to provide some rough numbers in the post, there are plenty of professionals here on BP that would be happy to chime in and provide more color. 

My advice is who you will be renting too. college kids big money from parents. your average Mr and Ms Joe who have a professional job with no kids etc. what amenities will you be putting in washer dryer dish washer etc.

I just finished a career as a professional ballet dancer in Aspen, Colorado but I have been coming to Portland for the last couple of years visiting my husband who moved for an opportunity here. 

I have looked at a few strategies to get started and the one that sounds the most appealing to me right now is to purchase my first property as an owner-occupied multi unit or a single with additional rooms to rent to local young professionals.

@Jason BocekIf you plan to file your own return - You should look into reading the following form instructionsSchedule E - supplemental income and lossesForm 4562 - Depreciation & AmortizationForm 8582 - Passive Activity Loss LimitationsHowever, you may be better off find a professional who can prepare your returns correctly and provide you tax advice.Your rehab expenses may need to be capitalized if it was paid before the property was livable.You should be entitled to other expenses outside of interest, taxes, insurance(remember paying down loan balance is not a deduction).You should interview a couple accountants here on BP.

I think you need to find professional company to help.

With that said, I think it's time to release the reigns to the professionals so that I can focus my efforts on growing my business.  

Have a discussion with a tax professional about how that works before you jump into S Corp world.From the rest of your investing, it is completely up to you as far as 'paying yourself'.

@Angelo Wong  as a real estate professional you can write off travel to explore new markets..

My focus is Hamilton and there's no shortage of amazing professionals,resources, and events to launch your real estate career.