Also, the owner expressed concerns over the capital gains tax early in the discussion...so I am thinking the opportunity to do vendor financing will help me get a good purchase price and help the vendor with taxes.  

The question is which one will have lesser of a tax burden.

Your current home would rent for $1800 and PITI (principal, interest, taxes, and insurance) is $1250.

. - the appraised value is super low, if you get what you are looking for, I would expect those taxes being significantly higher putting more pressure on the cap rate- it’s a beautiful, unique property.

Turn-key would likely be the smoothest, but I am open to a fixer upper if the numbers work.As far as the unique funding, I am an equities investor with accounts held in trust and therefore my taxed income is quite low which limits my options unless I opt for a portfolio loan or separate entirely through a DSCR loan.

Tax BenefitsSan Diego is an expensive market.

You can dig into cash flow projections, tax benefits, ROI calculations, etc.

It is always better to start with a multi-unit 2+ so that if something goes wrong, you still have one tenant to cover necessary expenses (mort, taxes, insur, etc).Also, major renovations are not a great idea for starting out as others said, especially out of state.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

IN Oregon. we have very few derelict houses or building very few.the one area north of downtown ( the old warehouse district) most all bigger cities have those areas.. the City put a 10 year tax abatement for repurposing the buildings to residential so buyers did not owe property tax for 10 years.