Where you live?

I'm an investor that lives in Amador county (near you), but I've struggled to make the numbers work for STR near me. 

It may be harder to set off the entire mortgage payment with house hacking, but any amount that you can lower your living expense is a win while simultaneously having your property appreciate.

I have never done a land trustWe have a living revocable trust that we set upHonestly I should have done it 15 years ago but did it like 6 years ago.I do not see the need for a land trust unless you are a politician, actor or athlete (someone who is famous).I have done business with multiple billionaires (not bragging but trying to make my point) including several that owned professional sports teams - and even they did not use land trusts…

Purchase price: $535,000 This will be a slow live-in BRRRR.

If it is simply the house and the tenant pays all the utilities, I personally would not charge more because you are renting them the house-not based on how many people are living there. 

Just a home that you rent by the room while living there?

-Current market rent is $1,250 per unitHere is what numbers look like when I live there: We currently pay $1,450/month in rent right now so that's something to consider.

I don't live off this cashflow so that alone doesn't bother me. 

My partner and I currently live in Brooklyn in a 1bd 1ba condo that we would like to rent out for about $1500/mth to a family member.