For one, the rental income tends to be lower than with short-term stays due to the necessary discounts, yet we still face most of the usual costs, aside from savings on cleaning and supplies.

In NYC the demand is lower in the winter but the supply is also lower so apartments rent fairly quickly still (typically within a few weeks).

Adding rooms does create the potential for more conflict but carefully thought-out floorplans, designate wet and dry storage spaces, and provide supplies.

In my professional opinion- supply currently exceeds demand throughout most of the city.

Are you going to supply the down payment and how much equity are you willing to give them?

I've seen insurance premiums for flood go up to 5-6k on a regular single family home depending on the area. 

Quote from @Marc Shin: For my STR, should I be using waterproof LVP or regular tiles for the bathroom floors?   

We would handle the guest communication, coordinating cleaning, minor repairs, stocking supplies, calendar management, etc.

@Jeremy HartwigYou are missing a lot of important data, such as median income of the area, rent comps in the area, what current values are.You are buying on actuals, but in many markets that have low supply and have a lot of demand, it makes it difficult buy based on actuals.

Sometimes large employers will rent furnished apartments for their employees coming to town on a regular basis.Also, if you believe strongly in the appreciation of the house, how bad would the negative cash flow be if you did long term rental?