I have begun to host REI Meetups in my local community.

I was in a mastermind zoom call and asked this question to Scott Trench (BP Money Podcast host and CEO of BP) and his advice was to house hack in the rapidly appreciating market.

If you come to Fayetteville I host a meetup regularly I have a very active online book club (not real estate though it's mostly philosophy, history, and economics)

There are also SDIRA Trust Companies that host educational and networking events specifically tailored to real estate investors.

I see that you host local REI events.

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

If you each make a bundle what will the tax be .

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. 

If you bundle the replacement toilet into a $7000 invoice for bathroom remodel, you may be stuck depreciating it. 

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.