My thoughts are to go ahead and pay my house off, which will grant me financial independence.

we've been asked the same question by a dozen or so good friends who live in/near SF about whether it's worth postponing the ownership dream, given where the bay area market is in 2018. personally, I think that right now is the time to hold off on entering the bay area market... unless you find a truly off-market, discounted opportunity through networking or a personal connections.sidenote: moving to the east bay (alameda, particularly) actually shortened my commute time into my day job in SF, compared to when i lived in SF. i'm sure you've heard this perspective before, but there's goodness to be found in the east bay, if you are dead set on buying in 2018/2019.from an investing perspective, there are still strong returns to be found outside of california. that's why we recommend to friends with capital that they consider looking into investment. that way they can start building wealth now and position themselves for buying that beautiful home when the time is financially right. sidenote: i recently posted on a similar topic on this thread. you can see if you scroll down and there are dozens of other helpful comments on this topic, on that thread: https://www.biggerpockets.com/forums/12/topics/587593-general-do-you-rent-or-own-the-home-you-currently-live-in?

Yeah, I struggle with the idea that I will be taking on a lot of risk both financially and working with newbies. 

Sometimes those losses actually put you in a better financial position if no personal harm was done.

Attorney will request this once you have signed the offer that stated SUBJECT TO REVIEW OF FINANCIALS/LEASES

Properties in Wellesley and Weston are roaring high in the past decade and sometimes makes more returns than a multi-family, and it is easier to keep its value when there is financial down-turning.I understand that it is totally a personal choice based on the financial situation of a family, personal preference, and personal understanding and sense of risks/benefits with regarding to such choices.

@Justin R.Your CPA is being moderately conservative, and your QI is being extremely conservative.Nothing is wrong with either approach - as long as you knowingly choose the relative safety of a conservative approach over the financial benefits of a more aggressive approach. 

A year from now I would like to own atleast 3 multifamily properties and have made it my long term goal to become financially free by the time I am 28 years old (5 years from now).

I often had distrust towards hospitals because I never knew what the amount I was going to need to pay would be after going to the hospital; and it always seemed to be hundreds or thousands of dollars more than expected.Thanks to the financial security that real estate can provide, I am in a different financial position now compared to where I was 4 years ago.

I will dig into the financials.