I am considering relocating to areas within a 1.5-hour drive from San Diego, like Hemet, CA, and am open to suggestions or feedback on suitable locations around San Diego within this driving distance.

Additionally, in your experience, when is it more suitable to hire a contractor versus a handyman?

Consider working with a real estate agent who specializes in investment properties to help you find suitable opportunities.Educate Yourself: Take the time to educate yourself about real estate investing strategies, financing options, and market trends.

For turnkey options it can also be a good idea to get ahead of the historical summer peak buyer push and not have to worry about getting a rental launched while most visitors are looking to stay for the night.For properties that require furnishing, the beginning of Spring is the optimal time for out of area or absentee investors to enjoy their property, familiarize themselves with their new home and their community and get operations and supplies dialed in. 

Small claims court may be a suitable avenue to pursue compensation for the costs incurred due to the undisclosed roof issues.

I have not seen a template though.I would start with thinking about all of the actions a tenant does (e.g. parking, visitors, taking out trash, flushing the wrong items, ect.).

You need suitable land to build that is zoned for multi.

Due to the passive nature DSTs are not meant for every investor and it is important to seek education to see if a DST is best suitable for you. 

Here are some of my thoughts:Use a construction loan, which would cover all the renovation costs -If yes, which loan would be suitable?

It's a very risky space teeming with fraud and not suitable to a new investor.