Is It Who Files First ???
1. If a property is sold to two different people and only the second one files at the courthouse, does that make the transaction between the seller and the first buyer null and void since they never filed?
2. Or does the second buyer lose out since the warranty deed they are holding is dated after the first buyer's warranty deed?
3. Would title insurance cover you in a situation like this, since they would not be able to find the first sale either?
4. Would the title company have to pay you if the first buyer sued? 
The answer to your question(s) depends on where the property is located. Different states have different rules for the treatment of this subject.
Every state has passed its own "recording act" for the registery of deeds. There are basically 3 types:
1) Race statutes: in so called "race" states whoever is the first to record the deed wins (i.e. wins the race of ownership) The first to record would be the record owner regardless of whether there has been an earlier but unrecorded conveyance.
2) Notice statutes: in these states a subsequent purchaser would be deemed the record owner of property only if he or she did not have notice of an earlier conveyance. In these states even if the subsequent puchaser is not the first to record the deed, they are protected so long as they did not have notice of a prior conveyance (sale).
3) Race-notice statutes: under a race-notice statute, which is a hybrid, a subsequent puchaser prevails over an unrecorded interest ONLY IF a) he/she had no notice of a prior conveyance AND b) he/she is the first to record the deed.
If you find out what kind of statute the particular state where the property is located has adopted you can answer questions 1 & 2. The title insurance company warrants to defend title against any "clouds" which the company has not taken exception from coverage. The title companies obligation to pay, if any, will also depend on the type of recording act adopted for the particular state.
Thanks, that helps.
I checked an old Texas real estate book I have from college. Found after the post.
It says that if the property is unoccupied, then it is the first person that files their deed would be the new legal owner.
It also states that if the property is occupied, then the purchaser has to visit the property and ask what the occupants rights to the property are. If they have not filed their deed but occupy the property and tell a potential purchaser so, then they would still be considered the legal owner even though they did not file their deed yet.
Thanks again for your help.
Glad to help.