Because the Adjuster's fee is normally a % of your claim payment, you may want to get estimates of the rebuilding costs and see how close the proposed settlement is before you decide if the Adjuster is worthwhile.  

FHA will also not loan on the house mentioned above because they estimate that the repairs could be in excess of $5000.

Is there a website that I can get an estimate on the re-hab price of xyz location?

That's how I would estimate it.

I am getting another roofer company to come out next week to give estimate on yearly inspection/maintenance. 

I have comps pulled, and my next step is to get a contractor/estimator out here to give me a better idea of rehab costs.

If you really want to go down that path, I suggest that you apply to work for a syndicator or RE Private Equity shop as an analyst or operator for a year or two, and browse through 100+ deals over that time period, underwriting each one, and trying to figure out, over that time, which ones you were "right" about, and which ones you were "wrong" about, as best you can.

Many have been burned by relying on their estimates.

Plus most hard money lenders will require a fair market appraisal.If you plan to rent, you already have that documentation plus the appraisal will provide estimated rents.

I'm trying to buy my first investment property with ~$100k saved up.My brother started his first W2 job last month that pays $45k/yr+ commissions.I plan to get a minimum wage job/an entry W2 job since I'm still in college and to hopefully qualify for a bigger loan.A lender estimated we'd be eligible for a $300k loan with $100k down, and a $2,500/mo payment on a $400k property with only my brother's income as of now.California is too expensive for us so I have been looking into out-of-state investment properties.What would be the best investing route for us to take to grow our wealth?