Multiple times I was called over to fix doors that had been pulled off the hinges, Outlet covers that had been pulled off and broken, towel rods and toilet paper holders pulled off of walls, stuff put down the drains causing back ups.

While I would rent it out as much as possible, husband would want us to block out 2-5 days/month there. 

We had zero regulation over STRs here for a few years when Airbnb first started back in the day, and truthfully it was bad: whole blocks of downtown were basically hotels for a little while there and it started to feel more like a commercial district than residential.

.), and a wonderful supermarket that is close by and walkable (2-3 blocks away).The reviews are excellent, and we are currently superhosts.

I dont have the full purchase price of this 4plex to invest though, so I would have to finance half to 2/3 which seems like a stumbling block. i can still make the numbers work, but at a much lesser monthly profit i suppose. i also dont have the w2 income to support 2 mortgages (counting the one i have on my house), so i assume any bank would have to count the existing leases towards my income which i understand is possibleI guess I was wondering about advice, or red flags, anything, on this specific deal.

If a guest spills food in the hot tub or fouls it, the cleaning crew will discover it during turnover and have to block it (no way to clear that kind of mess in a 4hr turnover).

@Joe Villeneuve Block Buster, Toys R Us, Sears, Kmart, and Borders all were corporate guarantees with solid credit at one point in time.

. :) Also, in a surprising twist of fate, a developer's just reached out to me and my neighbors as they're looking to turn this whole block into apartment buildings, I think.

Wrong, well two of them are in a part of dc that is rapidly declining & no one in the family wants to take care of (and he certainly cannot) and has deferred maintenance on both, the other two are beachfront and a block from the beach, one already got it by a hurricane (no damage, but did trigger a special assessment & insurance skyrocketed) the other one just being near saltwater for 70 years takes a toll on a place, the other thing that happen’s with real estate over time is appreciation eventually rapidly outpaces rent growth so these aren’t as big cash flows as you’d think, a decision is was made to keep these properties both for appreciation and of course stepped up basis (most of these properties he bought for nothing and then depreciated the hell out of) while he has great assets and it will all be fine in the ends and we are all very lucky he has the assets to cover my grandmothers care, frankly trying to figure all this when he’s 88 and everyone is stressed just isn’t ideal, he probably should have just 1031’d up certain properties that had environmental and/or let’s just say locational risk into new or very new construction in the easy to rent burbs like a decade ago, while the tax implications always make selling at tough proposition, I think at a certain point in everyone’s life especially if there are lucky enough to have kept properties for decades should transition them into these easiest assets they can find in their market (you can even put in a reit or more specifically a Delaware statutory trust) to make thing’s easier for them and their family once they are no longer capable of managing those properties themselves. 

They have removed me from the private fb group, blocked me from all social media, and will not allow me into the daily live office hours because I started telling people about this.