I have done about as much as I am comfortable taking on and am looking for some professional help for small misc projects. 

@Fred CanzanoIt really is time for you to get off the internet and onto the phone with a plan professional and your tax advisor. 

Should I bring in any professional appraiser as part of my due diligence?

My recommendations are to: 1) Hire a professional PM that deals exclusively well with lower end rentals (I can recommend a couple).

This will require some html and css skills at a minimum but unlike the previously mentioned hosted domains your code will be portable if you upgrade later.If you plan on designing something professional with some modicum of support you will end up paying something.

In our market it seems most professional painters prefer Dunn Edwards paint.

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.