@Kevin V. if I were in your shoes I would fix up the Carlsbad house and keep it as a short term rental that would still give you the freedom to use the property and keep it in the family while maximizing the rents you could get. Long term rentals are unattractive in CA imo especially since you can earn a lot more with different rental strategies even doing mid term rentals will still probably be more profitable than doing a long term rental.
As far as hiring a contractor or bringing in subs for each item that will come down to how much you want to be involved, you'll save money finding and subbing out individual jobs but it will take you longer and you will need to manage everyone you hire and contract to do business with whereas a contractor will manage all that for you but there will be a premium put onto the price obviously for that. So it really comes down to how hands on you want to be in your project.
