Seems like a bit less craziness than in the suburbs, but product with outdoor space, parking, bonus square footage is especially appealing nowadays. 

If you're appealing to people who want an escape from digital distractions or a younger generation that increasingly uses streaming over cable, then probably not a big deal.

I like scenarios 1 & 3 best, while scenario 2 is appealing because it might get you to where you want to faster, I put a heavy emphasis on having fun along the way. 

Many of my clients are looking at Lakeland as it is a steady growth market with good net migration numbers and the price-to-rent ratio is still appealing. 

@Malayna Brianna Nichelle Taylor, house hacking is a great strategy to get your feet wet with real estate if you do not have a lot of capital.A lot of offers now are either waiving the appraisal or submit form 22AD (Above appraised value) to make the offers more appealing to the sellers.

If that happens you can try to appeal, but when you have a recorded purchase sale price it's going to be hard to appeal.  

I have a small portfolio of Multi-family but the thought of leveraging my money <6.5 times by putting a 15% DP on a single family is appealing for long-term wealth.  

I have the vision and aesthetic in my head, and we're trying to make it super appealing for short-term rentals (our current STR is across the street and it's fully stabilized and doing very well).

Chicago has a rich culture and a variety of neighborhoods that appeal to all types of people.

Also, work on the curb appeal as that will draw in potential renters.Good luck!