I feel like renting out multifamily is what I may be looking for with this, if done right can give me cash flow, I can hire a property manager at some point and I am friends with a lot of home improvement companies, and I could either use some money I have saved up to put a down payment or home equity loan for some % I am comfortable with and pay both off as fast as I can and repeat.

I would recommend only using a short or mid-term rental house hack for a 2-4 unit property or a house with a detached ADU for your security and the comfort of the guests, which will make it more profitable.

Seeing as we are in Idaho on Lake Coeur d'Alene it is pretty easy to create comfortable and homey space.

Some people are not comfortable with older product.  

This would make lenders more comfortable lending to you, but it may be a harder sell for the family member versus just a promissory note.3.

Do you have a good relationship with your parents and are you comfortable collecting rent from them, addressing maintenance requests for them and things like that? 

If it were one of my tenants I would put in enough window units to keep the house comfortable.

I was initially considering selling my triplex and buying a single family in the bay area for the sake of aggressive future  appreciation while also giving a comfortable living with family but being a single W2 earner the numbers are still not making any sense besides future appreciation is highly speculative.So I was thinking if it would it make sense to buy a 12 plex in places like Oakland for around 2.2 mil using the sales proceeds of the triplex perhaps do a 1031 exchange.

If you are comfortable with that then you can always hold it for the long term. 

I'm still comfortable with LTR, MTR, and STR here in CO