The house needs a lot of work, but seems structurally sound with no signs of any major interior damage (mold/water/structural issues)- Is there a way to get a ball park estimate for what this house would need prior to contacting a contractor?

Get as much as you can, as long as you make a profit. yes, if the neighboring property sold for a certain amount per square foot then yours should be worth at least that. but you know he is trying to put a land puzzle together for a bigger development, so the ball is in your court. are you going to hold on to the property forever to see if the value does go up ?

I would check with your lenders "Crystal Ball" to see what he has to say.If you want to run the deal by me off line let me know.Good Investing.

I may just go the easy route and low-ball and see what interest I get in return.  

Contractors by themselves are not necessarily reliable as they may low ball the numbers in the hope of getting some work with you.

NASB with Jason Zook had an appraiser who low-balled my appraisal by using a city about 20 miles away as comps on a quad plex cuz nothing sold within 6 months in my city, instead of using comps from 12 months ago.

If they don't want to play ball, your best bet may be to refinance the whole thing now with someone who will.

You could also say this is a maintenance issue.The same tree with the branch damaging your roof is blown over in a storm and damages the house - this would be covered as it was a sudden event.Another potential issue is negligence - If there was a condition at the property that you were aware of and did not remedy it gives the insurance company an opportunity to decline to pay like the tree branch above.Here is two examples with very different results"Ex 1- If you knew there was an electrical issue and did not make repairs or delayed repairs beyond a reasonable amount of time and later that issue starts a fire...Because you knew about the issue it opens up for the insurance company to decline - they may pay or they may not so don't leave yourself exposed and make repairs when they are needed.If someone was injured in the fire they could claim negligence and opens up for them to come after you personally and violate the protection of an LLC.Ex 2- One of my clients furnace went out in his rental property and with below zero temperatures a pipe burst causing a LOT of water damage.

I have gained a lot of insight and motivation just by reading some of the threads filled with great experiences and information.I am hoping to start networking with investors, wholesalers, agents, brokers, lenders, property managers, and contractors, especially in the DFW area, to get the ball rolling in my real estate investing.

If you are going to make a low ball offer, day 1 on the market is not the time to be making low balls.