Fortunately historically the appreciation of San Diego has had a far better ROI versus better cash flow locales (verifiable fact).By the way rents on small rental units in San Diego have been going up ~$100/month per year for the last few years.

With multifamily you may be able to buy into a higher class property but most likely your down payment puts you in a slightly lower class property type versus SFR.

But I know house hacking is preferred by most people versus that idea.

Unfortunately this occurs when you highlight that you'll take pets (versus indicating "no pets"). 

I estimate a 25% - 30% cash on cash return on the property.I should have some depreciation, but I don't expect much amortization as I don't think there will be much in expenses initially.To me, this seems like a wise investment as I'll break even in year 1, but be way ahead in year 2 versus what the 401k would have done.Is the answer to my question simply comparing the Total ROI to my 401k withdrawal penalty?

Now I live in Austin Texas but mainly invest in west Georgia because I can get much better ROI there versus the overpriced Austin market.

I have contractors lined up next week to give me some estimates so I can accept, counter offer or back out altogether and give up my $50What's the point of as is with no seller contingencies versus listing contingencies?  

Also, renter mentality versus owner mentality .... owner will take much better care of the property.In some cases, payments received through seller-financing are higher than market rent.Some people have cash to put down but can't qualify for a bank loan.

It sounds like you're about to tackle that project and I would wager that the air infiltration will be greatly reduced or eliminated once you insulate the attic.

It can contribute to mosquitoes and overall tenant dissatisfaction with the property, but unless it is in your budget to fix I'd probably label it a bonus if you can do it versus a must-fix.