How do you plan to operate it?

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.

As others have stated, your fit & finish goals should be guided by whether you plan to:1) Rent: tenants don't always take care of a property, so you want to use lower-grade materials and workmanship.2) Flip: higher quality on workmanship and materials is usually required.Regardless, you always want to "Maintain to the Neighborhood".

If you plan to resell, I think it's wise to discuss with seller in advance and that way the lien on the property can be transferred to second buyer, but you can continue to make payments at the former schedule etc.

Off-market property is the best option for fix and flip, but since you are planning to live and flip, some on-market properties would also work.

I envision this portfolio supporting me during my retirement years—though I still plan to work, just in a different capacity than I do today.I recently finished reading "How to Invest in Real Estate: The Ultimate Beginner's Guide" by Josh Dorkin and Brandon Turner, which has been incredibly helpful.

The only time you would see a fee related to maintenance would be a project management fee if multiple trades are required during a property turn. 

At some point you have to make the actionable plan.  

The tenant refused to communicate about his plans to vacate and finally left the key under the mat on June 2 but made no communication, so we had to make 4 trips looking for the key.

To be honest, I´m in the Maintenance & Construction for corporate businesses for some US companies in Mexico and we do some Real Estate down here also, but it´s way much different than the US, so I have much to learn from a lot of people around here and as @Julio Gonzalez, I think this is pretty much the right pad and place to start and to break my fears to start all over again from scratchAlso, I´ld like to hear more from @Justin Brickman why he voted for his city, pros and cons, it will help to read from a local...As I said before, thank you all guys for taking the time to write in this post and share some experienceDo you plan to owner occupy. $40k will not get you a non owner occupied San Diego property unless you find some unlikely alternate financing.