Like Ori has indicated, the level of pain will be highly relationship based.

Those are more risk and a pain, but it was balance of $64k for a $1695/mo reduction in debt service. 

Also 4 units is a bit annoying to self manage, and those Mililani condos are 1970 construction, can't hurt to trade it into for brand new 2020 construction ;)That said, selling and 1031 was a pain, NOT passive, and moral of the story for me is don't sell real estate, ever, unless you have a gun to your head.

A royal pain, yes!

But some of them may not - while I'm a pretty sharp tool (pun intended!)

The winters are getting pretty brutal and their only getting worse every year causing them much pain with their arthritis.

A few neighborhoods that are walkable to the MARC train that goes to Union Station/metro in DC are:Mount Vernon and Station North (Penn Station)Ridley's Delight, Sharp Leadenhall, Otterbein (Camden Station)This isn't an exhaustive list, but I've seen some multi family homes over the past 12 months in the bolded neighborhoods. 

I also have OOS investments so would be happy to discuss the successes and pain points of the different strategies.

Contrary to the many pundits out there, businesses often have steep learning curves and initial costs.  2020 might be a "cash loser" but your scale and numbers should realign as you work through the growing pains. 

HOA's are a little bit of a pain BUT there are perks: water is covered, lawn maintenance is usually covered and you can count on putting the majority of your CapEx 'funds' at 0 because HOA's cover those kind of items.