Eventually he hung up on me as I had to keep asking him to repeat himself because the phone line was just so bad.

Mechanicals will go out, eventually. 

People that say constancy is key, are friggin demented.Do you think if NASA's spaceshuttle blows up, the director will say, keep launching them, eventually one of them has to make it to the moon?

I've ran some simulations and the properties are showing negative cashflow (-1% -2%) for the first 3 years, but then after year 3, things start to go back up with positive cashflow.I wonder if it make sense to take this risk, buy the home (with 20% down), maybe refinance later on (considering that the rates will go down) and eventually improve the cashflow?

Eventually you would want to pay off the balance or refinance your existing loan to pay it off. 

The whole point of going Airbnb over hotel is the kitchen for me, and I always end up with some kind of dull inadequate knife for cooking.

My goal was to eventually do a whole new kitchen anyway.

If you rinse and repeat, doing this over and over, eventually you will see you have the knowledge yourself.

Saving up more money over the years and scale slowly with 2 to 4 units and then sell eventually to buy something bigger? 

Then, you can start with renting out rooms and eventually moving out and having 1 cash flowing property.