And, as I'm sure you know, both investors would require a 3rd party verification of assets to prove their accredited status.Let me know if this is what are asking or not.

You're going to have to scrap like crazy to break even - think rent by the room, short term, mid term strategies that require more work.

It is pretty easy to keep it fully occupied but it does mean I turn away a ton of people who want a lease that doesn't quite fit my requirements. 

Success in real estate requires courage, perseverance, and the willingness to take calculated risks.Internalize these principles and apply them in your real estate endeavors, and you will be on your path to success.

The 8 unit has required more time and energy because it had been poorly managed for years.

If any of the proceeds touch the sellers hand the IRS sees it as taking profit and you will have to pay taxes on that portion.Net proceeds - Is the net sale, minus any Equity in home being sold.I find a lot of investors who want to purchase less than their reinvestment requirements will do the calculation to see what their tax burden would be if they purchase less than they sell.

that isn’t subject to higher down payment requirements or higher interest.

Create a simple spreadsheet or written list to compare the features of each and identify the ones that align with your requirements.

Requires some pre-planning if the ceiling height exists. 

I like both of your ideas so I would look for the single where an ADU is permitted or one with a dump ADU to renovate (that's best) and balance that against the purchase of a 2-4 unit.