I think you won't have a clear answer to your question until you identify two specific homes in each area to compare their details and your tax bracket.
Most of the time you cannot deduct Mello Roos real estate taxes assessed for local benefits and improvements, so you would want to know what portion of the tax bill is attributed to non-deductible MR in the San Ramon/Windemere home.
Brian brings up a good point about delinquent HOA fees, and Harpal underscores you are really at the mercy of the HOA Board. Personally, I'd pass on the HOA.
With Prop 13 at least you know your property taxes won't go up by more than 2% per year. While it is true that generally most of your Property Taxes (caveat being mello roos and other special assessments) are deductible on your taxes, the "true benefit" is equal to your tax bracket times the deductible property tax paid. Another way to describe this "tax benefit" is to say, using the example below, had you not paid $7500 in property tax as a deduction, you would have paid an additional $2,250 in income tax.
Sales Price $600,000
Loan Amount $480,000
Est. Annual Property Taxes (1.25% * SP) $7,500
Est. Annual Haz Insurance (.35% * LA) $1,680
Annual HOA $1,200
Income Tax Bracket 30%
Annual Tax Benefit of Real Estate Taxes $2,250
9 out of 10 times I recommend a single family home to my mortgage clients. You can be approved more by applying your capital to your mortgage rather than an HOA.
If you would like to discuss this further I would be happy to do so with you.
But, you will have to pay homeowner's insurance that is more expensive on a single (maybe), cut your own lawn, shovel your own walk, etc.
It depends what the HOA fee includes.
As devastating as the crime had been to the Sorrento community, I will say that the way many home owners have rallied together, in spite of the lack of cooperation from Toll Brothers and Massingham as alleged by some, is truly inspiring. They are not taking this lying down, and they want to make sure people throughout Dublin can learn from what went wrong, so what happened does not have to be part of a continuing trend.