Or put 20% down to avoid pmi and lower payments and find a roommate?

Or do you stick with hiring outside to avoid any drama in case the job is done poorly?

This is my first post at BP, but I have found the other resources and forum topics/responses to be exceptionally helpful and I'm hoping I can avoid some of the typical "newbie" mistakes. 

Good question, I usually assume 20% minimum to avoid being upside down. 

Another big aspect that will help you avoid vacancy would be to ensure you are renting your property at a reasonable rate, which you can determine by looking at what is renting or has been rented around your property!

As Charlie said, I would avoid the FHA route specially if you're planning on this being used as a investment property.

He would like to attempt to avoid paying capital gains tax.

There is only one problem I have with BP and that is many investors post how they would invest and what to avoid without considering the market. 

I avoid dealing with people like that.

My understanding is that reassessment can only be avoided by putting the property in a trust.