But before I even get into identifying specific properties, I need to first get smarter about some of the other things I put in my post. 

Without know more specifics, I'd suggest selling what you have now and investing in properties closer to where you live (and pursue 1031 exchanges).

One of the most important steps you can take as either a startup landlord or seasoned one is to use a platform specific to property management as it will elevate your operation and save you tons of time.The good news is that nearly every software designed for landlords includes these features.

So to answer the question specifically no I would not buy a property that did not cash flow and only for tax basis.

However, you could look into a “construction exchange” where the funds are used to improve a new property acquired through the exchange, but it must meet specific IRS rules within the time frame. 

If these continual expenses are not made  you end up with slum properties renting for a minimum weekly rate to transients.I don’t know your properties so I can’t form a specific opinion; however, based on the information you’ve shared I trust your opinion and knowledge.  

Specifically I think a lot about the smells that travel through the duct work between the units.

@David Lewis if you wanna chat rental rates and market specifics in some of the micro markets mentioned above I'm happy to.

Hello Doug, I am not a real estate attorney nor is this legal advice.Unless someone's state has specific laws banning contract assignments you should be fine doing the following.  

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?