Is it a situation where up and coming neighborhoods have low property taxes now but they gradually rise?

In additional to helping my dad (who would work himself to death before accepting financial support), I'm attracted to the tax and diversification benefits of RE investing, but a financial return is a secondary priority (because I think I can more scalably generate a higher IRR elsewhere).Responsibility breakdown: Given my skill-set, I'd run the investment models and likely oversee most of the tax/legal stuff but ideally gradually ceed control over time. 

You may need to calculate your time value to $20/hr starting out and gradually moving that # up as you see some success.The get rich quick schemes are an illusion, this is hard work getting things working right but worth it once the big ball starts rolling. 

During my stressing over where to buy I gradually discovered through sheer desperation, that Real Estate can be the ultimate creative space in terms of problem solving.

I have gradually taken over the management myself. 

Will develop gradually, in phases.

It is amazing how much easier it is- no more waiting on the post office, or listening to excuses about the check's in the mail...We did convert people gradually as leases were being renewed- I think all tenants really like it now that they are doing it- they have more options on how to pay- they can go to the bank and make the deposit or setup recurring deposits that are automatically transferred from their account to ours. and they get a receipt showing their rent was paid at the time it is paid.  

Every residence is unique and could be rented for different amounts for a variety of reasons.That said, I would gradually raise the rent over the years unless you are ready to rehab the place and then raise them up to market value.If you raise significantly, perhaps do some upgrade of significance to "give" them something as a result of the increase.

If they are quite a bit below market value, and pay on time every month, I would gradually increase the rent until it is at market value.

The person who is the good debtor will get dragged down by the bad debtor / deadbeat; when this is the case, the good person's credit report will have older years showing no derogatories but the occasional ding in more recent times, showing a gradual decline that can start to accelerate as more time passes.As a few other posts have noted, finding out their past history of paying rent is your best indicator; if they had trouble paying rent to past landlords, it can be expected to happen again.Lastly, I would add that you have to have a good understanding of debt to income (DTI) and how to calculate DTI and what a bad figure for DTI would be.