I walk a rental prospect in 15 min and know wht it will take to fix.- If you are financing, say NO FINANCING contingency. 

Not necessarily a deal killer, but you will need to find a commercial lender willing to underwrite you based on global income, experience, etc, and you will not get a 30 year fixed rate mortgage.

But I treat the home as my own, upgrade and fix it up to rent it.

2) how much will the subject property cost me to fix up?

I can give you many examples of where i've had to hire a second contractor to fix the first contractors 'mistakes/negligence' and in the end it costed much more. 

PLus usually fees are much less than hard money lenders and it s fixed rate for 30 years.

New investor, trying to find a fix and flip property in DC, Md., Virginia area.

Only minor issue in the last 4 years is one time they fixed something without using the home warranty on one of the properties (higher repair cost in the end).

Legally speaking, do I keep the money and tell Title to fix the problem on their own?

Honestly the Fix and Flip calculator in the Tools section would be perfect for what you need.