Buy and Hold in and around North West Suburbs

[Asif I.]

I am planning to start acquiring rental portfolio of SFR in and around North West suburbs. I have a full time job which pays well and would want to build a portfolio of cash flowing properties for long-term wealth building and "passive" income. Would like to see perspectives from fellow investors on the following:

1. Is Buy and Hold a better proposition in Chicago city compared to suburbs?

2. Are multi-family buy and hold investments better compared to SFR?

3. What are some of the best ways to acquire great Real Estate deals in the current "HOT" real estate market?

4. Should an investor wait for the market to "crash/correct" to get those great deals?

5. What are some of the best ways to find great property managers?

If you have similar goals, I would like to connect, please send me a message!