There is so many ways it can go wrong and being a greater negative for parties involved. 

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

Unlike our real estate investment, there weren’t hefty transfer fees involved in either the purchase or sale.

You mention not a fan of landlording, great, the bank never get's involved in that stuff right. 

- Get involved in local meetups2.

There is more paperwork involved with that option.

It involves much more than collecting rent or throwing up a Craigslist ad every blue moon.

This is a bit more involved, but as you scale, it is something you should consider.In response to your second question, I would say "yes" to allowing pets.

I have thought about Fundrise (medium success when I invested there), Crowdstreet (I have not invested there but might consider), farmtoghether (20k invested there already) and groundfloor (bad experience so not looking to invest there).Any advice will be appreciated.There is no greater wealth than peace of mind - Buddha - I have both directly owned real estate and passive investments in my portfolio.And if you're an accredited investor, then you have many options for investing in real-estate passively (and that don't involve all the stress of direct management nor putting money into public markets...which tend to be much more volatile).

Additionally, when comparing whether to build a single family portfolio or a comparable multi-family portfolio, you should also keep in mind the transactional costs involved.