I have no experience in real estate and I do not see myself working for other people forever.

If your intent is to have a legitimate transaction, then a contract protects both the consumer and the contractor.Most good contractors would be weary of a customer who refused to sign a contract for a medium to large sized job.

A few years ago I had 3 cars paid off (don’t generally like or carry any consumer debt), so I did cashout loans on them and sourced about $50K cash on them at like 3-4%.  

Few years ago I started feeling there is a need to earn more to support our growing needs perhaps with a second job but that would take away my personal time with my family .I got inspired with my previous landlord who was house hacking with a multifamily, started researching BP and started devouring every resource that came my way and took a big leap of faith and invested in my first multifamily without getting stuck in an analysis paralysis mode upon analysing few deals.While I do like the passive income aspect of a multifamily, I am feeling it's more than second job as it consumes me so much more emotionally and taking me away from my family and I sometimes start feeling if I introduced a new problem to solve an existing problem with this multi-family investment.I am generally a warmly friendly person but ever since I bought my first multi-family and started renting I feel like I have turned somewhat cold. 

Great as I'm not overleveraged at all, but I consume a lot of capital. 

After months of reading this blog and several bigger pocket books I have paid all my consumer debt off and am currently house hacking a row home in Baltimore with my fiance and a roommate.

Personally, I bought what I thought would be my "forever" home in 2014 and sold it in 2018. 

Depending on the amount of units you manage, there is either a good choice to go for the consumer type software that do most that you asked, or if you look for more robust PMS for a larger portfolio, Appfolio, Buildium, ManageCasa and Propertyware might be a good choice as their software is a lot more robust.

@George DespotopoulosI do plan to hold forever, but i do need to cash out as most are free and clear so I have a lot of capital tied up, enough to double my current portfolio size.

I find that whenever we reduce rent, tenants get the expectation that if you did it before - you'll do it forever.