Besides the questions I asked, please provide any input that you see beneficial in my situation.

Contrary to your approach of either making a purchase that benefits Dylan or walking away and ignoring the apparent needs of the owner, -what I proposed was lawful, beneficial to all involved, and much, much more caring than simply ignoring apparent need of another because it doesn't provide immediate and substantial profit. 

I am working with Mutual of Omaha and they have hired 2 AMC’s to get an appraisal.

Bad tenants are very difficult to get rid of in Ontario, and the PM only gets paid if I get paid, so we have a mutual interest in getting the best tenant. 

Brokerage IRA accounts buy and sell shares of companies, mutual funds, bonds, etc all the time so my feeling is that buying and selling assets inside of an IRA isn't an issue. 

It is important to look for a scenario that is beneficial for both parties involved.

When you’re considering purchasing a deal, it would be very beneficial to look at the P & L so you can determine what the average cost are by type.

It may be very beneficial to purchase a car that costs less and can help you on our way to financial freedom.

My only reason for skipping college would be if I found out I was better off avoiding the student loans and if it just wasn’t drastically beneficial.

They could do better with a conservative mutual fund.I don't know your market and whether any better deals are available, but I'd consider alternatives.