Short term rental permits are only granted to owners who will be renting their primary residence.

Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

So if conventional primary residence rates are that high, par rates on investment properties are generally higher. 

If you lose your source of primary income, do you have enough cash to make it through the crisis? 

i think this is a decision only you can make. im in a similar boat (house hacking my primary) and considering renting the whole thing out to get a solo home for myself. certainly a lot of appeal in that, given how much work goes into the house hack. but whether or not the numbers on cash flow align is up to you. personally i dont think $150 (seems like about 12%?)

If you can live a year in the property, I would recommend buying a primary, live there a year and rent it out afterwards.

It's been my primary with the business run out of the 3-car garage I built soon after getting the property.

The first step I did to raise capital was refinance my primary residence. 

That way you can put down as little as 3.5% for FHA or 5% for any primary.

Active investors absolutely have ability for higher returns, but at some point it does impact your primary job earning power.