Ideally, you do it for your single family, but I can understand the administrative burden that makes it a pain for a SFR. 

My partner and I had the biggest feeling of relief, satisfaction, and inspiration all at once.

Sigh  of relief.

If someone were to have 50 or more units to keep track of I imagines it would be a pain organizing everything as far as Wich tenant owes what and did they pay on time and considering some pay online some pay by check.

I feel your pain.

It'll be painful now but worth it in the long run. 

The biggest concern is structural damage; as any termites would cause cosmetic damage, the real painful issues are related to the structure. 

I know, everyone is always saying residential loans have better terms but they are also a horrible pain in the ***!

It was built on a hillside in 1876 so I feel your pain .

residential home and multifamily is two different things. you can control your environment with a lot of discipline. i recommend spending a good amount of hours reading and listing to podcast, then on your days off check out the properties you interested in investing. you can learn really really fast, you can be above average in a few months depending on how much work you willing to put out. also what is your financial situation, and how is that first investment do for you if it goes wrong. it is all relative, if your market is cheaper and you can afford to buy and hold without needing cash flow. there's enough tools out there you can quickly learn to minimize risk. if have a good profession, i would recommend buy at places not where you want to live, but areas that you don't want to live, it usually yield a higher return. i am not talking about the ghettos where they have shooting every night, but hard working class that just trying to put food on the table for their family. if you doing single family and try to minimize risk by doing your homework, you don't need all these people. just start slow, one person will recommend you to another and you will slowly find people that works for you. you can't build a team if you never work with them, you have to go through the pain of getting burn by people and you will find the one that will become your team. good luck!