Illinois requires a license to market aka wholesale more than one property per year.Are you looking to get into the wholesale game here? 

Hi everyone,I’m a novice investor currently managing one short-term rental (STR) that’s been performing well.

While the Fed looks to continue their trajectory of cutting short term rates, I suspect the mid and long points of the yield curve (particularly the 10 year, which is what most mortgages go off of) will stay elevated. 10 Yr treasury today is 4.4%, but if it goes up to 5% or 6%, your mortgage will likely be in the 8% or higher level, which then hits CF even more.  

A word of caution - this is a short term solution to mitigate the credit card load.

Short term, "higher cash flow properties/areas" will be better, but long term "better appreciating properties/areas" will yield a better return (in my experience).

I am new to the real estate game and got my foot in the door by purchasing my first property as a live in renovation.

I'm also in Eugene and have (or have done) flips, long- and short-term rentals, and multifamily.

All insight is appreciated :) @Deja Clark LOVE your willingness to jump in the game.

Your development deal will look much like a flip in the eyes of the IRS since it is 6-9 months as well you'll have the short-term side of taxes, not the capital gains taxing on it.  

Hi @Shan Randall,Welcome to BP and congrats on stepping back into the landlord game!