Because Airbnb only makes money when the guest books on Airbnb.Hence, they want the price to be cheapest on their platform, so people book on Airbnb instead of elsewhere, and want their properties to be able to compete with hotel prices (even after cleaning fee and service fees). 

Look at how people invested 20, 40, or 60 years ago.

Heck, some people might even pay more for the 'cool factor' of living in a 'small home'....I'd give it a go since you're a veteran of this RE stuff.

You'll learn what contractors are good at such repairs, and eventually people will start bringing you "problem properties" with that issue.Another related idea: contact a good local realtor and ask them if they know of any on or off market properties that would be a hard sell for most buyers. 

These people are not necessarily in the business of lending money and loans from them can be negotiated in any number of ways.

These minor details are the kind that distract people from the path of success. 

I know there are many strategies/tactics people have used... 

This is probably the thing that burns out people who self-manage more than anything.2.

It's people Bruce. 

I am completely new to the investing side and would love to find something to meet new people/learn as well as learn more about the city.