@Melanie P. is spot on.

They deal with 100’s and the IRS deal with hundreds of thousands, they’ll spot a mistake at first glance.

It just really bugs me when I have one of those tenants that are abusing the system and shouldn't actually be on Sec 8 and thus are taking a spot away from someone that really needs it to help get back on their feet.

@Doug Smith is spot on with his critique.

You're in the right spot.

Those are great spots, for sure! 

I mean once you talk to them, it's pretty easy to spot if they know what they are talking about.I've work on STRs before and to be honest, it is not the most fun aspect of accounting because the volume of allocating income from all sources (airbnb, vrbo, stripe, direct booking, and so on) to a bunch of random expenses (cleaning, supplies, repairs, advertising, commissions, and all typical real estate expenses).I had to strictly rely on the client's input on what the expenses belong to which property or even units, if the paperwork doesn't say. 

Ahmad,Everything @Alecia Loveless mentions above is spot on. 

About / Members – Neighborhood Building Owner's Alliance (nboachicago.com)Another great spot to check out would be the Straight Up Chicago Investor's Podcast website which keeps an up-to-date list of meetups as well. 

Luckily it is easy to spot under some scrutiny.Most people here just use Airbnb and VRBO and they collect and remit the payments for you so you are protected, but something to consider watching out for.