It never hurts to have an additional set of eyes to look after your property.

Additionally, consider operational costs like cleaning, staffing, and marketing, as they can quickly add up.For management, outsourcing to a professional property manager or leveraging tech platforms for bookings and operations could streamline things, especially if you plan to scale.

Here are a few ideas to explore that might help you get closer to homeownership in San Diego without selling:Cash-Out Refinance:Refinancing one or both of your El Centro properties could free up additional cash for a down payment without selling.

The cons as i see it include loosing the 2 of 5 year cap gain exception, typically not an ideal rental because the emphasis at purchase was buying a good home for your family and not a rental with optimal return (my ex-home consistently has the lowest cash flow for equity in my RE portfolio), not disconnected enough from the property causes addition angst on damage and may result in over improvement.  

In addition, yes there are property managers but very few want to manage my B or C class property for an extended period of time in the fashion I would if I was managing it or that a really good sponsor would.

Additionally, there’s always a risk that any pet-related damages could be hidden under furniture or otherwise concealed, potentially leaving us to cover the costs if the security deposit is fully depleted by other expenses (e.g., damages or unpaid rent).

Keeping pets requires a one-time nonrefundable pet fee of $200 (per pet) as well as an additional $20 monthly rent for each approved pet.

So you just need to look at that additional $2000 - $3000 of interest each year as really being 1000 - $2000 of total new expense to your after the tax deduction.3.  

You will be dealing with high school kids who are your employees...I know, there will be a manager, but a manager can only go so far...Plus corporate can come and make you change this or that, you will be obligated to comply.Seems like a headache to me even more than with rentalsSo Ive decided when I retire, I want to enjoy my life, not to deal with a headache from a restaurant

On the positive side, it seems like you have a good potential BRRRR that you can use to purchase additional properties.