I'd love to bail out on this property as soon as possible, but don't want to trigger any unnecessary taxes, of course. 

Just in principle, it's wrong to deter homeowners from improving or keeping up their properties by imposing big fees to do so. 

The other thing I didn't agree with is that if I'm forcing my potential buyer to produce a Cashier's check, I'm making them jump through an extra/unnecessary hoop.

I think that for many of us, property represents a physical constraint that imposes on our freedom to move from city to city or country to country in many cases.On the other hand, the financials of home ownership are so clearly stacked in favor of owning vs renting, that Millennials want to own for THAT reason.  

My real estate agent met with the sellers and took pictures of the property, and helped secure an end-buyer, making it unnecessary for me to ever view the home (other than pictures).Other Recent Posts by the Professional Investors GuildThe Role of Fear in Real Estate Investing - Friend or Foe?

After doing more research, I found that DORA states that a “Real estate broker” does not apply to any person acting personally acting as principal in acquiring or in negotiating to acquire any interest in real estate, or any person acting personally with respect to property owned or leased by that person....However, Article 1 of of the National Association of Realtors code of ethics states "Realtors®, when acting as principals in a real estate transaction, remain obligated by the duties imposed by the Code of Ethics." which includes all of the disclosure requirements.I found that the requirement to run all transactions thru the employing Brokerage comes from their rules that require them to monitor all transactions from employed brokers. 

I don't believe in taking risks that are unnecessary.

For many small landlords (and especially for investors who haven't done anything yet) it is an unnecessary complication.

., or anyone here on bigger pockets.For instance, they will go over the process of double closing, how is totally unnecessary and why only newbie wholesalers would consider it.

Especially since I will be a buy and hold owner, does the age of these properties create an unnecessary risk?