I am looking to meet a few realtor to help me access the MLS site to help initiate some conversations with the owners.

Conversely, you will run into people on your list that just seem to be a waste of time, so you’ll want to avoid them.

I am nearing the completion of a "skoolie" (bus conversion build) and am in debate over selling for a lump sum to help the fulfill my REI opportunities, or go the Airbnb route.

If you are going to change the terms of a rental agreement, you need all parties to agree or you need to wait until the current lease expires.Have a conversation with the current renters.

Good luck and happy to continue the conversation if you are interested! 

@Michael ClarkI'd have a conversation with your loan officer on that, and how strict they are going to be.  

So, if the tenants CAN stay then let them know that you may not end up selling it and have an honest conversation with them about it.If they CAN'T stay, then be honest with them about why you aren't renewing the lease.

Have you had the conversation about the collection/eviction process here in Cook County because it is crazy different then almost anywhere else in the country and I because of that we do approach things differently. 

For me, when I realtor tells me "You offer is too low, you are low balling", that means that they are either not investor friendly realtor or you did not have a conversation with him/her about your goals.

When you are talking to them, add to the conversation that you are trying to improve the neighborhoods where you are trying to invest.