Have quite a few out of state investors that we've worked with to get them great cash flow and tax savings. 

I would love to be able to retire my husband so he can join me on this journey.

Hi Jeffrey,It sounds like you're in a great position with your rental portfolio and cash savings, and I admire your commitment to keeping your investments!

So if the homeowner saves energy or goes on a long vacation, they still get charged 100%.

Virtually only ones to have not done well in San Diego RE were those over leveraged at inopportune times.If you want To invest in San Diego, I suggest you save more before starting.  

Today, that building generates enough passive income to cover his annual retirement contributions.You mentioned taking the 10% penalty, which I’d only recommend as a last resort.

My suggestions would be in this order:(a) Determine the type of financing you qualify for - this will short cut the process considerably and save time on investment angles and next steps.

Then I save that amount each month in reserves until I need them.

They might be able to save on fees going that route. 

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.