Airbnb has many negative connotations. 

A grand negative cash flow is not the issue.

The main problem with negative cashflow properties is this. 

You are speaking as though $800 to $1000 a month from one property is nothing.

If both houses were sold in 2024 then the loss will negate the profit from my understanding.

There were only three reviews about them on Yelp and they were negative as well.

Ask to speak with some of their current owners and current/former tenants.

I wouldn't consider it a heavy negative unless the street is super tight and parking is hard to come by or if the street is very steep/busy.The more desirable dense city neighborhoods it's almost kind of expected and off street parking would be considered a luxury rather than a necessity.If you get out into the suburbs I would say it's more of a big deal since more rentals have off street parking or a garage there.

It also negates the need for insurance - although that isn't our MO. 

If I remember you left your family in Vegas at a birthday celebration to come speak.