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There are apartments that allow you a shorter stay than a year, though the apartment prices are a bit high, I don't think that you will waste your money renting so that you get familiar where you want to be.

Showing a property in bad condition is only going to attract low-quality renters.

I’ve done some highly profitable “one off” deals in my 40+ years (and a few that turned out losers!)

Standalone brick and mortars like compass are the ones that are burning through money and taking it from the agent and customer it is very hard for compass to survive in those environment, as company like as big as amazon or apple move to hybrid work environment, the compass failed to grasp the spirit hence their transaction cost is so high.

The sky is not falling, but I agree if your carrying costs are high and owners did not budget earnings from last year to cover costs of the first slower months (Jan-May) then they are hurting. 

As for the quality, it depends on company. 

Wife and I have high credit score and we are high income earners (her W-2 & 1099 for me). 

Rates were low in 2018, sales prices were reasonable, and rents were high, so the numbers worked in our favor.

Selecting areas: Look for neighborhoods with high growth potential, amenities, and public transit when choosing places for house hacking, especially in big cities like NYC.