I will suggest you plan to House Hack a Duplex or Triplex or Fourplex every year for the next 4 to 5 years and you will thank me later.Goodluck man and keep us posted on your progress!

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.

Take care of work requests under $x?   

No I wouldn’t pay it and I would plan that potentially if I don’t pay it, they leave.

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.

I'm not too hung up on this, because the margins still appear very attractive (from what the agent speculated ARV). my hesitancy stems from a lack of experience and direct steps/plan of action to take on a property I like. 

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.

But assuming thsi is something you plan to pay back in 2-3 months the interest rate shouldn’t matter.

To succeed with the BRRRR strategy, focus on buying properties at a discount, work with trusted contractors, and plan for refinancing timelines.

Starting locally with multifamily and house flipping is a solid plan.