Although Josh makes a valid point about investing in your own backyard, it is not always feasible.

At the time, it was the only feasible way to get the financing done, as it was a portfolio lender from a banker I knew well.

Michael,Either one of the scenarios you have describe would work.If the property is not feasible by proximity or investment metrics to live in, the reasonable alternative that would not be in a war zone that could pay for her housing with cash flow would work.What kind of CAP one should expect in A,B or C areas?

Is 10-15% return a good/feasible return on flip projects for the business plan and projecting for potential investors?  

Paying more on monthly payments is the way I knew of it to be done, however, I thought there were different loans structed differently where achieving more equity faster would be feasible.

As a matter of fact, arguably, it's less of a headache maintaining it.So with that said, I was wondering how feasible purchasing rentals would be in Milwaukee, Indiana, Chicago, etc. for 25 - 40k and renting them out with the intent of positive cash-flow.  

Even if it isn't really feasible, asking -in a general way - if scheduling a visit in the near future is a possibility can give you a lot of info about how a provider treats their clients and how they prioritize new client relationships.

My recommendation if that commute isn't feasible for you would be to actually rent there and buy a house that will cashflow a bit further away.  

I've thought about the 1031 up when I sell, just not sure its feasible with the VA loan.

@Kevin Samuels  It's certainly useful to have a professional opinion as to the feasibility of a certain project but it does have its limits.