I see that you host local REI events.

I think as a first home it also clouds judgement so I appreciate any advise. 

Always helpful to have more seasoned investors like yourself.Where in Chicago are you planning to host your meetup? 

The gain or loss is ordinary income and can offset other ordinary income, like your day job W-2, interest income, unemployment received and a whole host of other items that reduce your ordinary income. 

Note that I can technically only rent out the side that I live on but I have spoken to folks in the "Austin Airbnb Hosts" Facebook group and as long as the property is registered as my homestead, they currently do not have the ability to track it I'm renting out one or two sides.

It just provides a hosting platform to advertise them for you and you pay them for that convenience.Completely possible to manage remotely, I have clients that do it all the time.

Anyway, I am posting because there is still some clouds in my head in terms of how to go about the rehab process.

While the dates are old, you can easily search for the 2022 dates for each host. 

It also means you'd be dealing with tons of one night, last minute bookings.The places along highways that I have booked which seem the most sustainable to me are separate suites in a larger home where the host lives.

Once you find a decent contractor, oftentimes they know other good sub-trades as wellAlso, if there are any local meetups in San Diego, I'd look to network with the hosts and see if they know anyone good.