Between the time associated with making the investment, tied up capital and associated stress involved, even if the investment breaks even or produces a small gain most would look back and wish the money sat in their account until a better opportunity presented itself.

A few eye-opening online searches will easily indicate if this is what you want to get into.

Another example of finding opportunity by being on site. 

If you put in the effort to source the right opportunity, you’ll find a way to fund it—even with minimal personal cash investment.It sounds like you already have the skills and experience; now it’s just about structuring the right deal.

Areas like Pilsen, Bronzeville, and parts of the South and West Sides offer opportunities for value-add investments, while North Side neighborhoods provide more stability but at higher prices. 

Hello all not sure if this is the right place to post this. but an opportunity fell in my lap.

Buy box: Location: Approx. 30 min drive to Boston Heights, for workNeighborhoods: Decent walkability score - not far from shops/restaurants/trendy neighborhoodsIdeal tenants: Close to hospitals/universities/schools for professionals/students/familiesBudget: $175-250K - Buying w/conventional loan, 5% down/ approx 20K reno.Property type: MFH 2-4 units - preferably side-by-side, with a yard we can fence for our dogUnits: 3+/1+ - better if 1.5/2 bath per unitTimeline: Plan to live there for 2 years, but possibly only 1 year if we find another investment opportunityGoal: Focus on appreciation - would like to see cash flow in year 2-3 (the year we move out), including overhead (Vacancies, Maintenance, Utilities) and budgeting in PM if eventually we don't manage ourselvesValue add: Opportunity for some forced appreciation, but not a full reno - cosmetic upgrades and updating kitchens/baths while we live in one unit.

I would say always be prepared to take action should an opportunity for house hacking come up!

This approach has not only improved our operational efficiency but also helped us stay on top of opportunities without getting bogged down by the details.Have any of you tried alternative strategies or found other methods that work even better?

Ann Arbor is my bread and butter, and is an evolving market with many potential opportunities.