This would still allow me to continue to invest in more properties, but it would still take about 12 years to pay off the house if I never refinance.3.

Property management is a pretty painful industry similar to general contracting... no one ever calls to tell you how grateful they are that the heat is working lolHere in Illinois, the answer is yes or you at least need to have a managing broker on your team as JW mentioned above. 

BP, I've been on a long search for technology and applications that allow me to automate parts of the tenant journey (leads, apt tours, screening, rent collection...).

I'm trying to build my team while i study more into REI. 

It's allowed me to do some of my own work like changing toilets and fixing leaking ceilings, but even if I don't want to do a job personally hopefully I'll have enough knowledge to not let a contractor over charge me, or recommend something I don't need.You'll also meet local contractors, and hopefully investors.They may offer an employee discount too.

Even better, if the contractor is able to attend/show up for the inspection by the township that would allow them to interface right on the spot and fix any small repairs.

As has been discussed ad nauseum, you will want to make sure code allows a short-term rental wherever you are buying.

Cooper) said that the mortgage is assumable (there is path that would allow me to remove spouse from mortgage and retain the current rate), but the process can take a while, is subject to fees, and they need to reevaluate my ability to qualify for the mortgage without my spouse.

2) If we decide to self manage, what are the things we need to do / what team of people we need to hire? 

@Jeremy Taggart Yes, positive about having to 'live there' for the lender to allow assumption of the mortgage.