Currently trying to isolate a market to settle into and focus on while figuring out why nothing seems like a good deal even though I keep hearing there are deals in every market (i.e., trying to figure out what I'm doing wrong while analyzing properties). 

The home appraised last year for 2.1m, currently on the market for 1.98.

How much of that is the addressable market?

I see that your location is Hawaii, I'm guessing the short term rental market is awesome there, so perhaps you could be an in person, boots on the ground for investors on that front.

I noticed the Chicago market has changed quite a lot since I started back in 2018.

In the past, I've found them to be good information for market insight and referrals. 

(with conservative assumptions on annual appreciation - 2%, and annual rent increase - 1%, as well as 5% vacancy/maintenance).I see so many people say they only go for properties with at least 15% cash on cash returns, which seems extremely difficult in this market

I just wanna make sure I’m marketing myself And making connections and doing all the right stuff.

The house is sitting on the market under the R-2 Zoning code as a single-family house not as 2 o 3 units.

The choice depends on your financial situation, risk tolerance, and long-term goals, with financial planning, market research, and real estate networking being essential.Good luck!