The history here is that when I bought the 3-family property 2 years ago in Chelsea, MA, the condo association for the property next door forced the previous owner of my property to move her fence about a foot so that they could park an extra car on their end. 

So in a catastrophic loss they are covered for what they put in plus some to help clean up the mess and pay for costs while selling plus a little extra. 

Many of them were still working full time, getting stimulus checks, or making a killing on extra unemployment.Now that the moratorium is over, they've dug themselves in a hole and reach out to government to fix the problem that government created.

It had strong rent income and some extra land.

To be honest, even though it was a big change of pace, it wasn't that difficult. I

You have to put in a bit more work but on higher-priced sales, it's definitely worth the extra effort.

If I were in your shoes, I would definitely get started with house hacking - buy a house with a low down payment (3-5%), rent out your extra rooms and either lower your cost of living or cash flow $$$, get experience managing your own property, and after a year, rent out your room and repeat the process. 

So the garage can flood from extra high tides.

If I have a good tenant who has done something extra or is having a tough time, I may knock $50 off their rent; but this is not a regular thing. 

After we submitted our offer the seller told our agent about extra expenses that he currently pays that we weren't aware of.