Our plan is a "Safe Harbor" plan which just means it's not very customizable.

I use FNBO Direct, an online & mobile bank, they have 2.25% right now which is decent, not the best but you want to keep your money safe especially if you're deploying it soon.

To be safe, I'd figure at least 6 months; 2 months for reno, 2 months on market, 2 months to close.Being such an inexpensive deal, there isn't a lot of room for error. 

Setting your financing question aside, as a general rule of thumb, you want to buy properties that are in safe, desirable neighborhoods because turnover is a cash-flow killer.

I thought South San Jose was safe and pretty much crime free.

Thanks in advanceYes you can under de minimis safe harbor.

You have to work out the math backwards by first establishing the max you can safely rent the property for after the rehab. 

I believe I’ll be able to obtain a HELOC plus I have a little bit of cash squirreled away.Question is, do I buy a place outright in cash that needs a moderate amount of work in an area that is to some, up and coming, but to others is not very nice OR do I put a 20% down payment on a nicer MFH with more units and put some sweat equity in (I’m really handy)Minus all of the nuances of investing, my concern mainly lies with, am I setting the bar too low by playing it safe by not getting a mortgage on a place?

I also like to do the math ahead of time so I can point out “you will make this much extra cash by seller financing” Always let them know they have more to gain in the transaction.I would also consult with a lawyer to make sure both parties are safe.  

My one fail safe is my home, which I own, clean and clear, through an inheritance.