Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

What creative strategies have you found successful?

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. 

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.

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!

There is some room for creativity here, but it takes careful planning and execution, and there is only so far you can push it before crossing the line from aggressive but legal to reckless and punishable.GROUP 2: Legitimate tax strategies, just not for the EOY to-do listForm an S-corporation.

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