do we even stand a chance of getting out hands on this to rehab and sell, or would you even recommend this big of a job for our first time (keeping in mind I work for an investment bank and would be very diligent about calc'ing out the rehab costs and keeping to a sound business plan)any help/criticism/opinions/etc.

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He wants to make payments to me for a 2 years (I talked him into agreeing to 1 year) spend some initial money on further improving the property and hopes to rent it out.

Any suggestions to improve the service and if interested in using the service, please let me know.Thanks.

The exterior improvements will be siding, painting and roofing.

you wont make money renting it out. just improve and resell

since you're estimating costs, ball park numbers are usually fine and this is what i would suggest doing to estimate repairs.if you're trying to do a detailed project analysis, you'll probably want the contractors to come see the property but you probably won't make any friends if you don't infact own the property yet because theres a good chance you are wasting their time considering how easy it is to lose a property to someone else before its in contract.

By THE HOUSE I mean the one that we weren't redigning in our head while we were writing the offer.In your shoes I'd be inclined to get a place in a (hopefully in the near future) "improving" neighborhood.