If he opts for a townhouse, a low HOA fee will help his buying power It gets tricky using lease agreement income when purchasing a house so I do not think that idea will work.

This is highly lender-specific; there are no universal guidelines for DSCR loans like there are for GSE/Govvy loans.

I highly recommend a book called Foreclosures Unlocked by Matthew Tortoriello and Kevin Shippee.  

cash flow is still fine with the high rates.

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.

It was high rent, low entry point area but within 6 months I dealt with an eviction and electrical issues.

Did have high quality photos/ great listing title and description?

And this low demand could be a couple of factors, either a rural location with low population density or the area incomes are not high enough in order to prevent a rent burdened scenario. 

Of the conversations I have had with people discussing hard money lending, some seemed opinionated in that the high interest rates and terms were enough to scare them off.

Would love cash flow, of course, but if I could at least break even on a highly appreciating property, I'd be happy with that.