Going to try and answer your questions in order...
HOW: Probably you quit claim the property to the LLC... but you might want to consult an attorney and you might want to make sure any lender is okay with transfer since act may trigger due on sale clause...
SHOULD: Probably your LLC would be a disregarded entity so it shouldn't make any tax accounting difference. A consultation with an attorney might give you insights into legal benefits of such a transfer...
DEDUCTING FUTURE REPAIRS: Assuming you meet the tangible property regulation rules for deducting repairs and you're not limited by the Sec. 469 passive loss limitation rules, you would deduct the repairs and get a tax benefit as soon as you spend the money. E.g., you place into service on Monday? On Tuesday, repairs (and other expenses) should be deductible.
REPAIRS WHILE PERSONALLY USED: These shouldn't be deductible when sold since as repairs they were never added to the basis of the property. There's symmetry here... you don't capitalize repairs for a rental... you don't capitalize repairs for a personal residence.
Hope that helps.