Hi Josh,
You gotta watch out for those red heads! It sounds like you have a lot going on. I agree you do need hustle, knowledge and money. Probably in that order. I have purchased many rental properties in the last 25 years and never used my own money. I bought my first property as a senior in college so didn't have any money and very little knowledge. I did have hustle. but keep in mind, real estate investing can allow you a LOT of personal time. I arranged my schedule so I worked couple hours in the morning during my daughters nap time, home with the family for lunch then worked a couple more hours in the afternoon. Later once the kids were in school I worked 8 to 3. For the most part, you can set your own hours.
I would offer a couple suggestions. First, decide where in Cleveland you plan on living and buy a 2-4 unit. Look for properties in good school districts that can return 20% cash on cash return. This will provide cash flow and the opportunity to learn your new market and the rental business. You or your wife will need to continue to work if you want to obtain a bank loan. Once you have 2 - 3 years tax returns s a landlord then you can consider going in full time. Remember cash is king and guard it with your life. Use OPM whenever possible. What ever you do, don't use all your cash. Maintain several month reserve for the 'Oh crap what was I thinking" months.
Second, I am primarily buy and hold investor. I have flipped a few houses though. If you are looking to maximize your time with family I would focus on rentals. The rent checks keep coming to you every month as opposed to flipping where you have to keep hustling to find the next deal.
Lastly, don't get to excited to buy the first property. Make sure the numbers make sense and keep in mind this has been a very long bull run in real estate. Make sure you can still pay bills if vacancy rates go up and/or you need to lower rents to fill empties.
Best of Luck