This property has been cash flowing for exactly 2 years.

I plan on getting a property every year until I retire if I can find a good deal that cash flows positively.I have a very close friend whose stationed in Columbus GA whose a real estate investor and owns rentals there!

An agent with market knowledge and deal flow that could present us with off and on market properties that match our strategy will be needed.

After 45 + years as a real estate investor, broker, lender, fund manager and syndicator, I’ve become aware that the “dream” of many investors and investor “hopefuls” is to be able to generate enough cash flow to live off their real estate holdings and accumulate enough wealth to make “work” optional.

I've narrowed down the best return for my money in this market to a 2 bed/2 bath (with top tier amenities) - about 500 total 2/2 listings.I'm finding myself a bit stuck when analyzing why certain properties are making so much higher than the average listings when they seem to have very similar locations, amenities, style, flow of home, beds/# of people they sleep, reviews, number of reviews, etc.

It's called Lifetime Cash Flow.

I think an investor can find a nice property there that will cash flow and potentially appreciate.My issue is that the OP mentions that she disqualified Baltimore because the city had a declining population but was still considering Cleveland and Toledo.From my brief research Cincinnati and Columbus both have had population increases.

There are more factors than just the community (#beds, level of theming, location to the amenities, style of home (single family, townhome, condo) and others) But I would strongly advise to stay within some of the same communities you mentioned like Storey Lake, Windsor Hills, Championsgate and a few others if cash flow is your goal.

The Japanese market is different in that it is a high yield cash flow market, non speculative investing.

I personally would stay away from condo-tels as they will be even worse and you'll have less opportunity to cash flow.