I suggest checking out some of the meetups on BPs meetup page:https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of all the other Chicago meetups that I can share with you.

@John Crawford awesome thank you I'll check it out!

It's always better to check with your brother's CPA since he has all the background, but I would say short-term rental with material participation requirements met by your brother, then do cost segregation.

Mine is a 2022 build  Hey Ryan, Your property checks alot of boxes for me for a MTR focused on attracting families as a whole home rental.Single story, Good school district, Little to no competition on Airbnb, No HOA.I bought a property once in 2015 and it barely cash flowed as a LTR but now 10 years later, I cash flow as a LTR about $600 per month. 

Last time I checked, the prices did go up.

If you have other area I should check out please let me know.

Appraiser will check the rent schedule and if there were any improvements done.4.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

For someone managing 1-5 properties you may be able to get away with checking up with it weekly. 

You would have to check the loan terms.