The waverunners are their son's. He's off at college, and about to graduate. So yeah, they have been sitting for a while. But he's going to be moving to (insert coastal city here) when he graduates, and going to take them back. Now how do you feel about the street? See, waverunners and things like that don't bother me, because they are transient. House sells? Boom. Gone. But the STREET itself? You said it was basically a glorified alley with a street sign at the end. That tells me that this may not be a city-maintained street, and that you and the neighbors may need to pony up the $5k/house to repave it... every once in a while. When was it last repaved? Who paid for it? Did Mr. and Mrs. Waverunner pitch in? Did they own the house when the last repaving was done? (This will tell you far more about their financial position. Any homeowner with a modicum of sense can get a loan for $5k. But if they own a house on the street and can't pitch in their part to repave... they are the Problem House.) Bigger Picture I'm with KB on the "Don't Buy Now" bandwagon. Trump is a fucking disaster. He's mercurial. Capricious. Undisciplined. And doesn't give a shit about anyone but himself. The US economy does not like uncertainty, and reacts poorly to anyone that rocks the boat too much. Institutional investors are holding their breath to see how bad it gets with Trump, but it's pretty clear at this point that things are not going to get better, economy-wise. (Today he started - kind of - a trade war with Canada over the lumber that is primarily used to build houses in the US. What happens to home building/renovations when the prices of lumber go up 20%? Right. Lots of construction workers out of work. And plumbers. And kitchen installers. And... shock to the housing market, which is already teetering at the high end.) If I could find a groovy downtown condo for a great price, I'd buy it now, and live in it for 5 years, and save every single penny I could. Then, after Trump has failed himself out of office and the market tanks, take that nice little nest egg you have built up, and go buy a house. And rent out/AirBnB the condo. BAM. Now you are paying your mortgage with your rental income, and you own TWO properties as the market recovers in a post-Brexit, post-Trump era of sober realism and a return to focusing on the fundamentals. My $0.02...