Building good habits that reflected the type of investor I needed to be to attain my goals (if that means not eating out as much, starting a side hustle, getting rid of bad debt, etc.).

In addition to the excellent answers above, I would add that you need to find out what constitutes the habitability laws in your state and make sure to answer those repair requests in a timely manner.

If you’re just going to buy a place with some people you know, it’s over engineered... and probably small $$$ anyways.The reality is setting something like this up, IMO, will probably do more harm than good in this case - it’s expensive, introduces execution complexity if you’re just a guy and some people, is difficult to explain to potential investors who are inexperienced, and takes focus away from the actual deal.  

In the long run you'll be better off and create good habits by learning to save money. 

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Make sure to meet the person and ask them the awkward/hard questions like cleanliness habits, noise preferences, etc before accepting them.

This would harm higher wage earners who invest for tax deductions.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

The answer is yes, you need to develop your own internal policies on what should be repaired out of pocket vs filing a claim.If you find lots of broken window type repairs, you are better suited to adjust your tenants or something you're doing to minimize the harm.

No harm in estimating worst case though.I think with expense estimates close to the norm, that this will look like a solid deal.