If you can sketch out what you want your website to look like and the flow/functionality, you can even go with fiver for cheap coders.

I believe Trulia had a map that had this information but no longer a functionality.

I'll try and use the search function to gather more information. 

Use the search function here on BP and you'll likely find a plethora of good lender options. 

So, does it improve the value and function of the house to have gutters or should i just leave them off of my rehab calculation?

This is where I would suggest making sure you have up-to-date contact information for all your tenants; and if possible, get all of them to pay rent online via the tenant portal (most software has this functionality.) 

You would start be calling the County Office and explain that he lived with his mama who recently passed away and he does not seem able to take the steps to function by himself, find a new home, etc. 

Should I replace all these things before renting out or just ensure they are functional?

In addition to the exceptional targeting (you can compile endless lists with your criteria) I got a lot of value from the other functionality the site offered such as viewing court documents (tax notices, divorce decrees, etc...). 

Be aware that every function and movement that requires labor or supervision comes with a cost and affects the total job cost.