If they are completely undisciplined financially then yes a 401K it helps them save, If they are more sophisticated and understand real estate investing for example and how it grows your wealth then they can reposition themselves into another investment beyond a 401K like rental properties.Here's the formula: knowing thyself X your own financial education X your own financial plan = YOUR WEALTHMy point here is that anyone can do well and be wealthy(working toward and achieving their individual financial goals, not society's) based on their ability to figure out how they can use their natural strengths and mitigate their weaknesses, coupled with the vehicle and plan that suits them best.

However, in my business we have to run consistence maintenance on machinery and we’ve used Wunderlist as a simple hack that has worked to schedule reminders. 

I agree a shell is best for large sophisticated tenants, but you are focusing on them as potential tenants only.

I’d love to hear your thoughts, and maybe even chat with someone who operates a sophisticated property maintenance plan

You do this with lower priced homes, you'll have issues, more than half falling out unless you hold their hand, educate them, monitor them and motivate them to cure what ales them.Having a CPA who got divorced and had medical bills, or any other sophisticated professional, who doesn't need a babysitter is a much better prospect.

It will give you a more sophisticated view than simply cash-on-cash/ROI.Finally, I think your expenses look a little low.

That makes me think these are not accredited investors and perhaps not even sophisticated investors. 

Hey Taylor....there are a lot of different options/services when it comes to rent collection, but it is usually a good idea to first consider the type/sophistication of your particular tenant(s).

CCIM would be useful for commercial PM and actually is excellent for working the numbers, although more sophisticated than the average investor Client makes use of.Also, you should be very familiar with the fundamentals of plumbing, electrical, and construction methods and processes, and the aging process of the various elements of typical homes in your locale.

The “workaround” usually being used by the more sophisticated “wholesalers” is whereby the end buyer is identified BEFORE a contract to purchase is signed.