Tenant issues are more likely to arise and then you have the owner....many aren't qualified expertise wise or financially to weather the storm.

BTW: most owners that have hired a PMC, don't want to speak with you, much less meet with you in person to hear a hyped-up sales pitch.Also, you want to do rental arbitrage - so, you will need to be properly licensed to manage properties you do not own as required by your state & local laws.- why would an owner want to do business with someone NOT properly licensed?

Soon I'll be purchasing my first ever investment property (Virginia) (MFH) and I honestly feel like I made a mistake.

Every attorney and experienced PM or owner operator say the same thing.

My primary interest is in small multifamily properties (1-4 units) priced under $300,000.

I would suggest finding those who are doing direct mail to note owners and get assets they can't afford.

As @James Carlson said, there are a lot of legacy unpermitted "improvements" to properties in the area.

A new owner would get to be a part of that vote.  

@Andy PtakLeasing agent at multi-family properties can be entry level.

TLDR: Quicken (quickbook’s little brother) is super easy, cheap, and still overkill for someone with less than 20 properties.