As for your Index funds, if you were trading indices such as SPX, you would have the favorable tax treatment accorded to §1256 Contacts:  60% of gains are Long Term Capital Gains, and 40% are Short Term capital gains.

He is a direct lender, not middleman broker fees. 

How do I find contacts for contractors and agents in Portland?

And if it were set up where everything went through a title company so the buyer pays the title company, they manage the buyer's loan (from me), and the title company ensures my mortgage is paid without my direct involvement... what parts of the transaction would feel risky or not worth the headache to you? 

Your cousin should contact the lender to discuss his options.If he rents it out, he must report rental income and expenses (e.g., mortgage interest, taxes, repairs, depreciation) on Schedule E starting when the property is placed in service.

The more mature platforms that are designed for landlords/property managers include Rentec Direct, Buildium, Appfolio, and Rent Manager.

What is an easy way to get in contact?

Quote from @Ricardo Lemus: Hi there,You guys probably went thru some of my post already and even help me with some experiences - Thanks a lot :)This time, after 6 months on this, I think part of my brain is saying that somehow I am in the right direction, and the other part is saying something is going on with the rent price I have set for my properties.

For what it's worth, this condo is technically owned by the the trust established by my Self Directed IRA.Thanks!

However, if you didn't get the results you're looking for, please contact me so we can help and do right by you.Again, I appreciate all commentsI'm an open book and my truest desire is to help.Thanks.