That could be risky too but otherwise for 2-5 months out of the year I could be breaking even or in red. 

@Jahangir Hasanovthose low price points are tempting for a reason... probably lots of deferred maintenance and potentially in more challenging neighborhoods.if you think you're going to buy a random property off Zillow and start cash flowing in month 1 or even year 1... buckle up.i strongly recommend you start with a house hack locally instead. 

Even a house hack is super tough in the city now.

Even then my stock performance was dismal compared to RE even considering investing a lot more in the market.

Since much of the house would be common areas, you might even consider hiring a cleaning service to go through periodically.

The insurance company was pretty reasonable to work things out with even though it did not start out that way, and they did have my blood pressure up considerably!

The cost of eviction is really high in NYS, the cost of mismanaging an asset is even higher. 

Hard to answer what to look for without even knowing what you're trying to insure - there are a lot of types of rental properties.Landlord and homeowners insurance is not the same though the types of coverage are similar.

After acquisition, we had gone on to discover that this property was even more ideally situated than we had previously realized.

From a lender's perspective, that type of loan would be so incredibly complex that it would have to really be worth the lender's while to even consider doing it.