Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookConsider checking out HUD homes for small multi's owner occupied gets first crack.Download BP’s newest book here some good due diligence in Chapter 10.

Having a handy man background will help you to estimate the cost to rehab properties (even if you don't do it yourself.) your military service will give you access to VA loans.

Can someone give me a over estimated costs of holding and closing for a 250k property.

Get estimates for repairs and then include that in your purchase cost and run your numbers.  

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookConsider checking out HUD homes for small multi's owner occupied gets first crack.Download BP’s newest book here some good due diligence in Chapter 10.

There were many stories of millionaire real estate investors at the end of the book who prefer to have paid off properties rather than accumulating as many properties as possible.  

General Rule of thumb to use for SFR, but can be a quick guide for what you're looking at..1% for A neighborhoods1.25% for B Neighborhoods1.5-2% for C Neighborhoods2+% for D Neighborhoods.Not sure of the exact location, but I would venture to say you're probably in the C range in Madison and the way she is charging tenants/ vacancies.As-is with vacancies I would estimate $390,000.Completely Occupied / No major deferred maintenance $590,000.I'm curious to see other peoples thoughts on this too..

I do however need an investor friendly realtor and contractor on my team to help me with comps and repair estimates to help me determine my offer.  

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookDownload BP’s newest book here some good due diligence in Chapter 10.

Also, you need to get a solid repair estimate as well.