How does association pay for street repairs, assessment or loan?

We are a 27 unit association built in 1966. We are looking to completely redo our street for the first time. Up to now we have made do with patches and sealant. But the street is crumbling quickly. We will have to do an assessment to pay for the redo in order to not use all our reserves. Looking for other associations who have done this type of large project and what are the dos/don'ts. Also, the loans that are available to HOA's - Do they require the board members individually to assume liability for the loan since that is something that is unacceptable to the board members.