Hi Chris,
This has been a very interesting post to read and I love the willingness to dive into the jumbo deal. I'll let you know I am relatively new in the investment world; like you a long time reader. Through my education about real estate I would love to learn a little bit more about the deal.
CONSIDERATIONS: Things I would heavily consider is how you will get the people in to rent the property, being away for so long I hope you have built property management into the expenses equation as BP always points out. The home does look impressive from that picture, but as you mention it looks a lot like a "Real World" (the TV show) house or a playboy mansion, than a traditional home. This could be a great benefit because it is unique or it could limit your target market, especially with the higher cost per night.
My other concern is that by attracting a more party-like crowd, they could leave a party-like mess and big damage. Nobody will treat your home like you do.
FINANCING: I think the financing piece is interesting. Obviously you wouldn't be able to get a conventional loan just yet as it would require $300k down. The path I would choose is to find the help of an investor if you are to do the deal, hopefully through BP. I think by having equal investment in the house, you would both be able to take responsibility for the deal, and if they are local to the San Diego area they would be able to monitor the activity of the house, including cash flow, tenants and property managers.
The next place I would go would be a hard money lender. However, being away for 190 days a year and not having a large real estate portfolio I believe that would be difficult to get funding. I still believe finding a partner/mentor would be the best route.
EXIT STRATEGY: What is your end goal? Make sure you know the answer to that question. In my real estate investment I know that my end goal is to have passive income and completely pay down the mortgage until I deem it time to sell. That's easy to say with small multi-families.
From the look of your post it seems that you will use this place as a primary residence when you are state-side which is a good idea, just remember how that may impact cash flow. Also, 5 to 10 to 30 years down the road, are you planning on selling the property and retiring? Beware that the property my be difficult to sell. I know it is price below traditional houses in San Diego, but it is not a traditional house either. Keep the end goal in mind.
On a final note, I do not want to seem pessimistic! I love the fact that you would like to take the money you've made and work it to ease your work life and create more financial freedom. I just want to make sure that you make the most wise investment for your position. I would start a little bit smaller and grow my portfolio, but I also am only able to obtain smaller loans at this point in my investing career. From an outside perspective, this could be a great investment for you or it could be a money burner and a headache. Make sure you run all the numbers and understand the time and effort investment you are making. I wish you the best and hope you find the information and network that you need to make your financial goals come true. Look forward to seeing the outcome!
Joe