If I meet the other financial requirements will lack of multifamily experience be a deal killer? 

Never talk to them about financial literacy. 

Now any other time I would automatically reject a candidate for having an eviction, but I am thinking if I should reconsider given boyfriend's financial background.

I intend to actually invest with a mortgage on my second property only if I do go through with buying this one with cash.I do appreciate all feedback as this is probably my biggest financial decision to date - if you strongly disagree or agree with my plan PLEASE let me know as I need to make a decision soon.Thanks!

Most of these homeowners are in some sort of financial duress and are depending on the sale to rectify their situation.  

They have the right to make it one and will, depending on how your financials look as you report to them every year. 

I know the bay area fairly well as i grew up there but less confident about the financials side since I'm new to multi unit investing.

I started a journey back in 2015 towards financial freedom with a goal of acquiring 50 units in 3 years time, and yesterday I was able to acquire a 19 unit value add apartment building in Berwyn with my partner @Scott Skinger With the 19 unit acquisition, I have gone from 0 to 52 units in just over 3 years time.Not only have I reached my personal goal of topping 50 units, but I also get an opportunity to re position a desirable asset in a growing neighborhood.

We're working toward financial independence so the question really comes down to increased cash flow vs. decreased liabilities. 

Spending an hour with a CPA who understands your overall financial situations would be time well spent, but there are some general rules of thumb:If you hold the asset for less than one year, your profits are considered short term capital gains - which are taxed as ordinary income at your standard tax bracket rate.