If you are newer to investing and would be willing to live in the same building as your residents, I think considering a house hack could be a good place to start and learn. 

I would recommend you either purchase a single family residence (SFR) and rent it out. 

For an investment property you'll need 20-25% for the down payment vs 5% for a primary residence.

Plus after the 2 years, you avoid capital gains tax on the profit under $500k and get the ability to use your VA loan for your next primary residence. 

Currently costa Hawkins makes single family residences exempt from rent control.  

However, there’s no set rule on how long you must hold the home as an investment before converting it to your primary residence, but it’s generally advisable to rent it out for at least a year to avoid raising any IRS concerns.

I understand how if you live in a state where you can implement penalties for late payment (this is day 11 now, so today she is out of the mandatory grace period) it may be easier to incentivize residents to pay on time (in Florida, where I live, they start eviction proceedings on the third day after you are late), but in areas like Baltimore that are more tenant-friendly, what do you do to incentivize people to pay on time?

You should take advantage of the personal residence tax benefits.

Investment Info:Single-family residence fix & flip investment.

Investment Info:Single-family residence buy & hold investment.