How do you choose a market to buy your first property?

[Rahul Srivastava]

Hey everyone, total newbie here to real estate investing. I'm 26, single, and I want to begin real estate investing to supplement my stock portfolio and grow my net worth to get closer to my goal of financial independence. My job is fully virtual, so I can live anywhere in the country but I will not get a COL increase. I'm currently based in Miami, FL and I want to leave this city and find a property elsewhere. My plan is to buy a single family home and live in it for a couple of years as I save more money for a down payment on a new home elsewhere. 

My main issue is that I'm not sure when & where to buy. I can buy pretty much anywhere in the country and while I know some cities that are not going to work but that leaves most of the cities in the country open to me. I'm looking for some advice to point me in the right direction for the following: 

1.  When is a good time to buy? 
2.  How do you narrow down a housing market to buy into? 

If it helps, my main goal is to generate cash flow so that I can save that and use it towards a down payment on another property or funnel it into my stock portfolio. I currently have about $25k saved up for a down payment & other expenses (including closing costs, and any repairs). I plan to buy summer or fall of 2022 and I will continue saving until that point. Looking to save up between $40k-$50k. 

Thank you for reading, I appreciate any advice!