You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

You may want to make an introduction between your CPA to those 2 colleagues.The CPA can go over their services and pricing to your colleagues.I partner with many people on real estate deals - It never gets to a discussion on whether they do their own tax return or hire a professional.If a partner mentions he will provide capital - does he provide the capital on a timely manner.If a partner mentions he will find deals - does he find many deals and provide an analysisIf a partner mentions he will manage a property - does he manage the property well(find tenants, collect rent, communicate with contractors, etc)

I agree, with turning the property over you have to make it ready, account for vacancy and go through the courts for an eviction, all of which will cost you.

FlashlightTape measure/Laser measurePaper/Pen/iPadBinocularsReceptacle testerLevelMarbleDroneRespirator/Face Mask/Eye Protection/GlovesAQI testerWater pressure gaugeThermal cameraEndoscope cameraKnifeI bought over 20 houses in my lifetime and I’ve never taken more than a flashlight. 

The place I have is over 30 years old and a mansion ("mansion" in Japan means an apartment, not "mansion" like a huge house). 

And you are looking at an interest rate around 7% instead of over 10%. 

Sloan, he seems to be knowledgeable about commercial real estate and after peering over his website briefly, it seems that he offers personalized training to people new to the business. 

I've been working in software consulting services for over 15 years and it's kind of disheartening that I haven't been able to figure it out, but I've got other things to worry about (like how to get a few more properties so i don't have to worry about buggie tech crap anymore :) ).

Investing in the right neighborhoods can increase your odds of success.Also if you look at the appreciation rate in Cleveland and Dayton over the past 10 years its actually quite similar to the cities of Columbus.But I do see your point of being careful in "declining population cities".

Quote from @Paul Whitehurst: Many will tell you to borrow money from Property A to purchase Property B, but that's known as over-leveraging and not recommended for a newer investor.