Hi @Kevin Chen!
Welcome to BP!
Here are a few answers for you:
1. There ARE deals on the MLS, but you have to be willing to be glued to it so that as soon as the deal hits, you're ready to act. Or, better yet, you'll need to look at deals on the MLS with this mindset: "I'm going to offer on 20 properties on the MLS per week, knowing that I may only buy ONE property anywhere from 2-4 months after my initial offer." There are deals out there, I've seen them. But the likelihood that you're going to buy one the first week that it's listed, without competition, is slim to none. Competition is high. You'll need to learn to offer on a deal, and TRACK your offer for weeks (and sometimes months) in order to get it where you need it.
2. I think looking for SFR's is not a bad idea for passive income. It's tougher to scale than MFR, but they're more plentiful deals, AND you can still get a great return on your investment.
3. I don't have a whole lot of experience with the tax sales. Perhaps another BP member might be able to shed light on that. However, I do know people that purchase tax sales, so I know that it can be lucrative IF you know what you're doing.
4. Why wait for the market to "cool off"? The time to act is NOW. The truth is, it will never be the "perfect" time to invest. People make money in up-markets and down-markets. It could be 10 years before the market cools down enough for you. The secret is to know which investments are good in an up-market, and which ones are good in a down-market. Your strategy will change depending on where the market is in the cycle. Even though the time to act is now, you still will need patience. I'm not saying to buy the first thing you see. But, you need to start offering on deals (a lot of deals) now, and then track them so that you can buy them at the number it makes sense at later. Make sense?
5. 1% rule is not unrealistic in Chicago. Depending on the area, you can get much higher than 1%. It's just that, most of those markets that do better than 1% are in the south side of Chicago. I'm positive that there are good returns in many other areas, but I've seen some ridiculous numbers down there. But you HAVE to do your research. The deals are out there, the HARDEST thing that you're going to learn in RE investing is that finding them is the TOUGHEST part of the job.
Hope some of these answers help! Feel free to contact me if you need anything else! Would be happy to help you out.
Best,
Van