I largely lived paycheck to paycheck, drinking away the weekends to avoid the overwhelming sensation that my life was slipping away from me.

You can put a mortgage into a "trust: without triggering a due on sale but again contacting your bank/lender is the best route to avoid any issues.Some banks/lenders or servicing companies change guidelines and even a trust may require other paperwork but the attorney usually facilitates that to be safe.  

They can help you navigate the market and avoid common pitfalls.If you’re serious about taking the plunge, start analyzing properties in both Boston and Chicago markets to understand local trends.

This is 100% the most misunderstood aspect of rental income. 

Working with Real Estate ProfessionalsLocal Real Estate Agent: Choose an agent experienced in student housing.Property Management Services: Consider hiring a property manager if you’re not local.Inspection and Appraisal: Conduct thorough due diligence to avoid costly repairs.6.

Are there issues that you think you should avoid regardless of potential for discount? 

By making partial dispositions, you can also avoid subsequent recapture on these items when you go to sell.

I'm not counting those since I don't manage them, but I typically avoid cities and states with laws antagonistic to landlords.

Avoid them like the plague. 

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success.