I usually talk to a dozen banks when preparing to make an offer or just get a property under contract. 8 unit is just south of 20 by the fairgrounds.

So unless im prepared to lawyer up 3k just to try and get some of it back the answer "just walk away from your deposits, im trustworthy" doesnt work for me.I have prepaid for work from big names, Lowes installs etc.

I'd share that if I did, I'd be prepared to pay them to vacate.

If the water would have came back bad we were prepared to replace the pipe but was told this repair would be around $8K. 

You just buy as many as you can and then figure it out, there is no way to prepare, you just deal with it.

How can I best prepare for managing two rental properties, including handling maintenance, vacancies, and tenants?

Congrats on preparing your property for an STR in San Diego!

Without reserves, they might be unable to evict tenants or prepare the units once they are vacant.

As a former planning commissioner the people AGAINST projects are the loudest so you want to make sure you have a good pulse on what your neighbors and the louder people at public hearings stand so you can be prepared ahead of time. 

Understanding the risks associated with any investment, being prepared for the worst possible outcome, and having a plan for when an investment doesn't perform as expected is essential.