Anyone may issue a 1099 even if you are not required to. Whether a landlord is required to issue a 1099 for repairs made to their property depends on the type of business that the landlord is operating. Also, before issuing a 1099, you need to send a W9 to the contractor to collect their tax number. They may indicate on the W9 form that they are a type of business that is exempt from the 1099 requirement.
The difference between a repair and an improvement is it a repair restores the property to as was condition while an improvement adds value to the property or extends the useful life for the property. Assuming you are correct that your foundation repair is a betterment, you add it to the cost basis of the property and then depreciate it. This isn’t double dipping because when you sell the property, you pay depreciation recapture.
