The problem I keep running into is that I live in Oregon and I may be wrong on this but it seems like most properties are overpriced and are more speculative appreciation plays, like in the Portland market.

We continue to get tenants relocate from other states and attempt to play the Covid card after the first month. 

So again that income comes into play on the next one round.

Also as mentioned earlier, the down payment is not mine and will be paid back at 0% interest so I'm slightly confused if cash on cash return plays a big factor in this deal since once they're paid back, I won't have any cash in the building.Thank you so much for any insight and help with anything I may have missed!

Zoning, land use, and the parcel's history all come into play.

Personally, I just want a small, tiny start, just to get on the playing field.

If there happen to be a "tenant" that had a very loud sound system that played heavy death metal 24 hours a day would that be breaking any laws? 

Many methods will not return that original investment any time soon.. it will be out there working for you, but could cease to be liquid for long periods of time.So visualize your money going into each of the methods you have mentioned and tell me what you would see playing out over the next year or so.

So once we played it as “it’ll be a lot easier if we buy a house we can house hack, live there a year, simultaneously scope out other areas of town we would prefer to live, stack cash, then move into our long term house and keep the other as a rental and continue to subsidize our mortgage payment that way.”Was a no brainer once we looked at it from a logistical standpoint rather than wanting to be in the cute HGTV home right out of the gate.

This keeps the playing field even since I am incentivized to accept other tenants who I don't have to pay the fee so this keeps their clients on a level playing field.