These solutions can make a huge difference, and the long-term option will really help set your STR up for success.

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.

And sounds like a good set of options you are looking at.Here's some data and visualization on recent trends in some of the markets mentioned here.

I have two options.

The spacious primary suite features a private full bath with double vanity, while the flexible layout provides options for bedrooms, an office, or hobby spaces.

I'm happy to discuss it further with you (I have appointments this morning, but will be back after lunch) and there are a ton of options now.

And while a 1031 exchange isn’t an option, some people explore alternatives like installment sales to spread out taxes or even tweaking the investment structure so your returns are treated as interest instead of equity.There are definitely some creative strategies out there. 

Here are a couple of ways you could structure the deal:Lease Option with Seller Financing: You could lease the property with an option to buy later, allowing you to rehab it while giving the sellers time to find a 1031 replacement property.Seller Financing with Deferred Payment: Structure the seller financing with no immediate payments, allowing you to refinance once the property is appraised, and the sellers can complete the 1031 exchange when ready.Escrow Holdback: Transfer the deed into an escrow account, giving you control without immediate transfer, so the sellers can take their time with the 1031.Third-Party Facilitation: Use a qualified intermediary to hold funds and facilitate the 1031 exchange while you refinance.These options allow flexibility for both you and the sellers.

I'm happy to chat about your options to see if we can get you out of this mess. 

Most 1-4 unit real estate investors are using DSCR loans right now for any buy and holds while flippers lean on higher leverage bridge/fix and flip loan options with higher interest rates.