So there are multiple benefits to contacting the listing agent directly, 1 I don't flood my agent with petty questions, 2 It is much quicker to ask the questions that are missing from the listing. 3 I can tailor specific questions per property. 4 There is no back and forth which limits misunderstandings.

You can get into the properties quicker.

Longer story, we've always invested in apt buildings but are looking to make some "quicker" money in the short term with the $100k we have available to spend. 

This is one of the quicker ways to build wealth and it fits a single lifestyle really well.

But a title search is cheaper than a trustee's sale, quicker too.I really don't give a carp about him and his problems. 120 late pays over 10 years (honestly!)

We have no other debt.My thought process is to pay off the rental property with the smallest mortgage as fast as possible with our extra cash flow, then use that rental income to pay off the next smallest mortgage of another rental prop, and finally when that property is paid off we want to use all the rental income to pay off our personal residence quicker so we can retire without this giant mortgage payment.

This makes it easier and quicker for you to evaluate deals.

You get a quicker sale because the buyer can literally visualize EXACTLY how the house will look.You'll find REALLY cheap and Nice stuff on Craigslist.com & your price can cover the costs.

It will clear up much quicker this way - 10 to 15 days then by just allowing the system to clear on its own 90+ days.BTW, as TC said above live and learn.

I would hold and rent.I am not familiar with the market in your area, but I wil take a stab at it and say it is not a sellers market.A few months or years and the market may change allowing you to sell quicker for more money.Plus, you know this property intimately making it easier to maintain.