I wanted to generate enough passive income to be free once and for all.

They're more likely to be extremely picky and may end up being a headache down the line, but that's something you'd have to gauge on an individual basis.

We are not looking to make the most amount we can per item (because there's so much) and are not looking to spend time putting individual items up for sale. 

That being said, I am looking for individual investors or small businesses that would be willing to introduce their business to me and perhaps let me "tag along" on some of their current projects, negotiations, walk-throughs, etc.

Having your money sitting in a bad investment, hoping for it to generate unknown returns at some point in the future, is not a good strategy.

Eventually I would like to generate enough passive income to retire.

-Field food will generate sales tax for the city, which is a plus since all that money was going to the county previously.

Now I have to transfer the lots into individual names paying the transfer fees again.

Preferably it would be the 4plex so that as cashflow is generated you can continue to work on the 5plex.

It is never wise to think of time as individual packets.