we have to be prepared to buy 30-40 houses before winning one.  

Don't think you can rationalize paying credit card APRs with this strategy and end up ahead.You can get significantly and consistently better returns from your investments than you will lose through depreciation.

And the statement "That is not me" is a (Warning flag, Red Card, Strike 3, 15 yard penalty, 15 minute major, Technical Foul, pick a sport reference you like....

Get some business cards and pass them out to folks.  

*You need to have a rental criteria *You need to have excellent curb appeal *You need to have an appealing open house, application forms, good setup, with card table and chairs, pens and paper, receipt book, etc.

In this case, you would have a hard time winning with the wording that you copied above.

I’m not really sure how to proceed because it seems like there’s an inherent conflict of interest here for the contractor: they have an incentive to keep the estimate low to minimize the payout from the insurance carrier and win the bid from us.

The consequences are weighed and some win and some lose.

If you dont have enough cash reserves set aside before you make the investment you might need to look at cash from credit cards that can be paid off when the property is rehabbed and stabilized and refi'd.

I've had pretty good success charging my tenant's benefit cards (MasterCard stamped).