The principal sum, plus all accrued interest, as defined above, shall be paid to the Holder upon as set forth herein.Payment & Due Date: The Maker shall not be obligated to make any payments ofprinciple during the term of this loan until January 4, 2024 ('Due Date"), at which time the entire principal balance, plus all accrued and unpaid interest, and other charges, if any, shall be immediately due and payable in a lump sum balloon payment to Holder.Collateral: This Promissory Note shall be secured by a mortgage lien against thefollowing real property: Address listed; (the "Property"), executed by Maker for the benefit of Holder.Assignment: This note is NOT assignable by Maker without the written consentof the Holder, which shall not be unreasonably withheld.Default: The occurrence of any of the following shall constitute an "Event ofDefault':Failure to make any payment due hereunder;Nonpayment of principal upon the Due Date;The breach or failure to perform any of the terms, provisions, conditions,promises or agreements in the Note, that is not cured within five (5) days ofthe date of written notice from Holder;Any representation or warranty made or deemed made by or on behalf ofMaker to Holder under or in connection with this Note shall be materiallyfalse on the date as of which made;

I have a condo that has been a rental for the past 8 years, has performed well in downtown Chicago.

While it doesn't meet the 1% rule it's in a stable, desirable area that'll perform more consistently for you over time so it's worth the tradeoff in my opinion.

You bet, but not active or pre-foreclosure.

To be safe, consider starting with standard percentages or slightly reduced figures until you have reliable data on the property’s performance.

Specifically:What square footage ranges are performing best?

It is hard to get information on performance online. 

Unless you are doing a serious amount of volume , both from a cost and performance aspect, it will make more sense to outsource.

I didn't see a lot of the cross-portfolio-performance I'm looking for. 

I bet there are some ways you could proactively plan so the problem almost resolves itself.