If you go that route you need several documents to protect you and effectuate taking over mortgage payments (POA, notice to release, etc. )If you only have a strict 90 days to do this then in your agreement that should be spelled out but several things depend on your relative and how secure he wants to be in the fact that you will basically hand the house back over to him at the end of 90 days if you haven't sold it.

Every landlord should make it a policy to not only evict bad tenants but also follow through with small claims. 

Your locality will state which rules specifically you have to follow, but if someone applies but does not fit your criteria (So long as your criteria doesn't discriminate against protected groups), then you do not have to rent to them.

and yes City of Portland is extremely strict with the short term rentals, they even go on the airbnb website to look for operators without a permit.

Either way try and follow the 1% rules, which means these days you'll have to find value.

I've been following Bigger Pockets for some time now in the forums and the podcast.

It depends on if IRS considers you an investor or trader. they look at different factors, I pulled court cases where they looked at these:(1) the taxpayer's investment intent; (2) the nature of the income to be derived from the activity; and (3) the frequency, extent, and regularity of the taxpayer's securities transactions (Kay; Mayer; and Moller)  A taxpayer is a securities trader only when both of the following are true: (1) the taxpayer's trading activity is substantial; and (2) the taxpayer seeks to profit from short-term swings in the daily market movement, rather than to profit from the long-term holding of investments. 

That link is for an article I just published here on BP that spells out the details of how you can meet this requirement easily and cheaply.As always, make sure you have a competent real estate attorney on your side if you choose to follow through with forming any kind of legal entity or agreement (like a JV Agreement or Limited Partnership).

My main reason for considering commercial is because 1) the duplex and triplex and even 4plex market in my area is very competitive and it drives purchasing prices too high. 2) I guess I’m kind of a pretty ambitious guy and my wife has followed my lead and trusted my guidance and I want to help our growing family (2 kids and 1 on the way) meet our financial goals as fast as I can!

As for my numbers they are as follows.