The right market for you depends on whether you prioritize cash flow (Augusta, Columbia) or long-term appreciation (Greenville, Huntsville).

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

I have one rental property in San Marcos, CA (North County San Diego), which was my primary residence for several years before I moved to Orange County.

Focus on LISTINGS!

Since you’re already diving into BiggerPockets, focus on clarifying your investment goals (house hacking, multifamily, or BRRRR), building your network with experienced investors and lenders, and most importantly, taking action by analyzing real deals.

Trying to understand what multi family rentals are and learning how I can invest or convince myself to invest into it or learn more on this topic to understand this is not my path.

-My fiancée and I are planning on having our first kid by the beginning of 2026, so extra room would be ideal as we are somewhat limited in the primary residence. 

My thought is to take a compiled list of property addresses saved in Excel and then run data scrape from Zillow and Redfin on each of those addresses, pulling the property details back into excel and into the appropriate table I have set up. 

They often have different vendors introduce themselves so you can build your team and they often have a local member do a case study on one of their properties to share the ins, outs, ups, and downs of the investment.

Wish I would have done more of these earlier on.