Generally, note investors try buying at a discount to increase the yield, but there can be exceptions.When you buy a note you are not buying the property securing that note, don't go down that road, you are a note holder.The more savvy types, like myself (khmmm) can acquire notes being financed by the old note holder, they sell at a discount, finance the sale of the note as that relieves them of credit risks, risks of foreclosure and loss, payment administration or servicing issues and slow pay issues.

First find out if there any additional liens on the property.Second if you think its something you want to buy have him contact the lenders to give permission to you to talk to them.Third come up with an offer amount that works for you.Fourth let the lien holders work out who gets how much.Fifth you or I are not lawyers and he may get a 1099 in the year that the property sells to show the balance between what is owed and the sale price.

You would need to see all motions, court rulings, have a knowledge of property's value, secured and unsecured liens, other properties owned by the debtor, entity in bankruptcy, marital status, division of marital assets, condition of property, indication of debtors intentions in bankruptcy, quality of the prommisory note and mortgage or deed of trust, strength of supporting documentation, timliness of notices in relation to note, whether property was owner occupied at time note was originated, priority of other creditor liens, ruling tendencies of presiding judge, foreclosure laws of the state property securing note is located in, respones file by note holder, whether and amount of bankruptcy protection payments made, whether debtor has or will attempt a 'cram down' and whether it will be a principal reduction cramdown, an interest rate cramdown, a term cramdown, or a combination, whether debtor plans to challenge the legitimacy of the lien, expected legal fees for creditor, etc.Once you are familiar with this information you can begin to evaluate a value for the note.

Realize most of the Chicago BP investors are keeping up with the news but just in case here's a recent announcement made by the Mayor's office working with the major banks in the area to provide relief to landlord mortgage holders whose income is affected by COVID-19. 

The money could also help pay for moving costs and assist mortgage holders and tenants with payments after the moratorium expires.

I then arrived to the US as an au pair in 2014, got a teaching job that would sponsor me right after became a teacher with an H1B visa and here I am to this day.

Can’t help but feel I’m the bag holder buying it at the top.

Current debt holder.

At the end of the Final Judgement there is a notice in bold and underlined print that says "If the property is sold at public auction there may be additional money from the sale after payment of persons who are entitled to be paid from the sale proceeds pursuant to this final judgement"A third party bidder was awarded the auction but doesn't the mortgage holder have first rights to this property?

@Andrew Johnson, are you yourself a buy and holder?