PM fees are high, exactly because so much work is required in managing STR.  

Most who respond recommend creative financing....seller financing, sub to etc. or using highly levered hard money debt. 

With a dynamic real estate market, diverse neighborhoods, and high rental demand, Chicago is a fantastic place to invest in house hacking. 

There are several lenders that will lend 80% of the appraised value, but for that high leverage point, most (if not all) lenders will require an appraisal. 

However, here are a few strategies to explore:Local Real Estate Investor Networks – Join local REI groups, meetups, or Facebook groups where private lenders may be open to funding primary residences under the right terms.Seller Financing – If the seller is open to it, you could negotiate a seller-financed deal where they act as the lender.Community Banks & Credit Unions – Smaller local banks may offer portfolio loans with flexible terms.Wealthy Individuals / Family Offices – High-net-worth individuals sometimes fund private deals, especially if they see strong equity and repayment potential.IRA or Self-Directed Retirement Accounts – Some investors lend money from their self-directed IRAs for real estate transactions.Since you’re willing to pay higher interest for a short-term solution, a contract for deed (land contract) might also be an option, where the seller keeps the title until you pay it off or refinance.Would you like me to connect you with any potential private lenders?

There is always risk, and these are highly risky and regulated techniques.

20% is not high for managing a STR.

I do well, at least enough to go on vacations as a family, put money into high yield savings accounts, max out the ROTHs and add to investments when I can with money saved in savings and checking accounts.

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?

.• I purchased a small 1B/1Ba condominium in a high rise building in 2004 for personal use.• In 2010, I moved out and decided to put in in service as a rental unit.• I was able to keep it well occupied and leased throughout 2024.• I sold the condo unit in late 2024 for a nominal profit.That brings us to today.