For now, my goal is to earn an additional $2,000 a month of passive income (after expenses) within 3-5 years from now, in addition to my regular income.

Tenants would be your regular blue collar, in metro Detroit we have the big 3 so very good employment with future growth and very well paying jobs.

We stopped collecting late fee and reduced the rent as we were all facing difficult times and agreed in writing once the states opens up we would return to regular rent payment as stipulated on the lease.I required some documents from him to confirm he was out of work and his document showed he's been out of work since November.We've not received any rent since March, i reached out to him and he complained he was holding back rent because there are things in the property that needs to be fixed threatening to call an inspection officer to the house.

Shop around and you will find that some require $1k-$2k to start, while others may open it for much less if you establish automatic regular monthly contributions. 

If you find a duplex-4 plex for that price or cheaper live in one unit for at least a year to qualify for fha. you will get better interest rate compared to a regular conventional investment loan AND YOU WILL BE HOPEFULLY GETTING YOUR MORTAGE PAID AND SOME EXTRA MONEY IN YOUR POCKET EVERY MONTH.

If you can't find a regular real estate meeting, start one! 

I understand both of these are a bit more hands on than regular buy and hold.What systems/strategies do you use to minimize headaches?

A letter of intent wasn't necessary on these smaller deals and you can use a regular realtor and submit offers just like you can on 1-4 unit properties.

@Joe BeYes, you can purchase a probate property through the regular MLS purchase that includes not only using the regular purchase agreement but also the probate purchase agreement.If you do send marketing material to attorney's remember that the probate attorney represents the PR (Personal Representative) and the PR represents the estate..

There are still houses in these areas that you can pick up for 100K and a 50% Delta (margin of Rehab Budget, Fixed Expenses, and Profit) is a totally attainable number depending on your skill level as a rehabber/ project manager.