My childhood best friend’s parents are selling their house and I am wanting to do a buy and hold rental with it but finance it with owner finance.

You and her pay no taxes on the sell as the Trust paid the taxes.I sold 3 properties under my parent's Trust and the Trust paid all the taxes on the sale. 

My question is for the furniture that is in the house and clothes and anything else that could be donated does anyone recommend a company that comes out to do site pickups.

My parents are pretty supportive and will co-sign with me.

If you choose this route, you could also look into creative financing and getting parents to cosign on loans.

We started a parent company in Wyoming but we do most of our investing in Tennessee. 

Tyler,You're not going to cashflow while living in your house hack in LA unless you do something like convert the garage to an ADU right away.However, it is possible to reduce your cost of living (assuming you're currently paying rent and not living with your parents)  while building up a lot of equity through principal paydown and appreciation.Best,Jon

I know a few people ages 30-40, they work, but zero ambition to do more because "well, eventually I'll get a couple million when my parents die."

Looking to break into the market in either Capital District or Glens Falls, NY (I'm from Saratoga Springs and my parents live in Glens Falls, NY).

Hopefully that happens to the property I'm looking at 🤞Unfortunately I don't have the money for a down payment right now...I'm planning on using a private lender (my parents) and then pay them back by refinancing after a year