So I would suggest keeping your STR property geographically close and doing as much as possible to keep your profit% high as possible.As far as the actual house you use, I would just say - be honest, be fair and strive for the best area, most amenities, cleanest house, best communication, and any other extras you can get.

Again, this topic can be discussed AT LENGTH as well so let me know if you want to go further into it.My suggestion to every new investor is to trust your instinct. 

My current agent suggested if it made sense financially, to do some rehab work to get the properties rent-ready, but I do not have the liquid funds to do so and sell these as-is.

What markets would you suggest looking at?

I would suggest focusing on solving people's problems more than trying to sell them.

I would suggest doing these separately however since you will run into issues with a partial release clause on a blanket loan.

Any suggestions on where to look other than the facebook outreach I've been doing?

I like and appreciate both of your suggestions!

Or like many small in businesses you raise cash from friends family and anyone else that knows loves and trusts you.The other thing I suggest is to make that $27,000 or $37000, or $50000 yourself over the next year. 

I love that you have specific goals for 2025 - I believe if we think it, write it, say it, and share it our goals are 10x more likely to come to fruition.Are you able to do option 2 and just house hack a 2-4 unit building and use a renovation loan which allows you to put down 3.5-5%I highly suggest getting to some local chicago meetup groups (we have an in person one on the 17th)...here is BPs list: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.