I'm concerned about jumping in late, buying an expensive house with all of the learning curve that comes with and realizing I could've made more money buying another 4plex or two...

Hello BP Members,We are most concerned with the Portland laws favoring tenant rights rather than the landlord?

Feel free to contact me with any questions and concerns. 

My main concern is the current cost of supplies and labor shortages.

Any pro tips on partnering with friend, what expectations/rules should I set in place from the start, any negotiation leverage given I might have more responsibilities and any concerns on partnering with someone who doesn't hold citizenship or greencard in US?

I am just concerned about  trying to make the 1031 timeline work for an asset type I haven't worked  with before.

Most people are concerned about rent raises so in a recent fill of two units Month to month which I haven't done before I made it clear the property was available for year round occupancy and the intention would be annual raises. 

That being said, I am more concerned about your assumption that putting $5,000 into the property will result in the $35k value increase you have in the calculator

He has other cash flowing properties and lives a frugal lifestyle so he does not seem too concerned about replacing the income from this property or have much plan for the proceeds of this sale.

I also share @Scott M. concern about the lack of deposit.