I know a lot of Chicago investors are here too; but if you were in my spot would you recommend Chicago as prices are too high and I have never been to the city moving next year.

I am not familiar with how HELOCs work but they declined me saying my DTI is too high.  

Having the contractor relationship in place to move quickly and provide a high quality renovation at a reasonable price.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Its proximity to campus, turnkey condition, and rental history make it particularly appealing to investors seeking high cash flow and low vacancy risks.

Focus and consistency are going to be your best friends.Also, I wouldn't tackle buy-and-holds right now unless you currently have a high cash flow revenue stream in place.

If I create a debt fund that offers 9% interest on first lien notes with a 5-7 year payout, would that be attractive to high net worth investors?

Fees seem high but could potentially be worth it.

Ironically, high income earners can make more passive income through tax mitigation than they can through buying high cash flow deals in nearly every situation. 

.- High risk - Time-intensive - Requires substantial capitalBRRRR:Pros.- Builds long-term wealth - Generates rental income - Increases equityCons.- Complex process - Requires financing - Dependent on market conditionsAirbnb:Pros.- Potential for higher returns - Flexible pricing - Short-term commitmentCons.- Requires active management - Subject to regulatory risks - Income can vary seasonallyI wish you the best in your new venture.