With $500k used as down payment, over the last 3 years I could easily have purchased 4 properties totaling 92 units and had a bunch of that 500 left over for coffee for life.

As to whether a $50K deal is a waste of your time for your ROI I would say it's not and a big part of that is because it would be your first deal in the area, the first deal is always a wealth of knowledge so what you won't make in $'s you'll easily make up for in networking, contacts, knowledge of the area, etc.

The second story unit can easily be converted from a 1BR to a 3BR to maximize the property, but I would have to add heat to areas that are currently not heated in the attic.I am thinking instead of dealing with radiators, that I should convert to electric baseboard heat.

My goal is a second vacation-home in Seattle near downtown where we can easily Uber/walk, whereas the majority of the time it'll be Airbnb to pay down the mortgage.  

@Brad Noe recently relocated to Lexington from Pittsburgh...anywhere I can drive easily from Lexington, so Lville included...I'm exploring and learning the area.

Most people think they will be in a lower tax bracket in the future because they plan to downgrade their lifestyle... this is again incorrect money myths that are so prevalent.By taking you money out early you will incur a 10% penalty but if you understand how you can easily get 20-30%+ returns in real estate a year that 10% penalty is nothing.

I think I could easily write out procedures for receiving work requests, sending letters for late rent, obtaining bids from contractors, etc. 

You could easily fall into the trap of being a nice guy and letting rent get behind only to find that you now need to evict someone and will be out even more rent. 

For transit purposes, you can get anywhere in the country fairly easily. 

You can easily (I guess that is an assumption on my part without knowing where you live) find someone here on BP who you can pick their brain for the cost of a cup of coffee and figure out best steps as you get started.I have owned about two dozen homes in the area this house is listed and I can tell you that the challenges are real and they are steep to making a passive investment work in this area.