If you want more detailed advice, I can provide it.You BEST option is to contact a bankruptcy attorney and find out your other options.

I will be start out on my real estate journey soon by working for a company and sourcing deals for them.

However, I am unfamiliar with any lenders having traditional mortgage options for anything with a VIN number such as a trailer.

Durham on the other hand is a great opportunity for investors seeking more short-term growth, more options, and higher likelihood of cashflow. 

IF so then Furnish Finders might be an option for Mid-Term rental.  

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.

Especially in a more competitive market where the options are plentiful.

If you find you are unable to raise the money for an all-cash purchase, switching gears to Fannie will only work if you have a LONG time to close in your PSA or have many extension options (which usually require more hard earnest money.)

If you do go the seller finance route, consider asking for a right of first refusal option in the event the seller ever decides to sell the note. 

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.