Great comments on this thread- I’ve been house hacking for cash flow for the last 2 years. While the cash has been nice I have friends who have made more money than I have through appreciation in higher price point neighborhoods (Ukrainian village/wicker park) they bought 2 flats for $600-700k and have made $100k plus in appreciation. Meanwhile my two flat in back of the yards has almost doubled in value but My equity gain doesn’t compare to theirs.
If you like your day job and have a pile of cash I wouldn’t be afraid to increase your price range and dump it into a quality asset up north. You’re gonna make a bunch of money in appreciation over the long haul plus you get to live in a nice place which won’t be hard to sell for top dollar.
I like looking at the “profit if sold” portion of the bigger pockets calculator- you’ll see high price point properties generally have better returns but less cash flow (as John Warren mentioned)
If you have your heart set on value add and have more time on your hands I recommend the HUD 203k loan. That's what I did with mine and I love the product. Hit me up if you ever want to talk about that type of loan. The strategy is only better if you are looking to minimize your cash investment though