Naperville SFH vs Chicago (Condo, SFH, MFH)

[Tyler D.]

I'm looking to pick up a lot of rental properties this decade. My strategy is going to be focused on long-term rent appreciation vs short term cash flow, so I will be buying in nicer areas with a focus on rent appreciation over the next 30 years.

I like Naperville for this reason, as it regularly tops rankings for multiple metrics, but has houses available in the 400k range.

I also like the idea of buying in Chicago. The idea of buying condos downtown seems enticing, but it looks like the HOA fees really hurt the math. MFHs seem ideal, but there are almost no good options available. SFH are an option as well.

What do you recommend as the best area/ property type to focus on?