I would have a lot of options and a lot of the stress I deal with would be alleviated. 

Now use Guesty- not ideal but good enough. 

Has anyone had experience purchasing property from the city and developing a new house on it?

$250 Million Apartment, Office Project In The PipelineAUSTIN (Austin American-Statesman) – Capella Capital Partners is developing North Gateway Plaza, a $250 million multi-building project at 10615 Burnet Rd.

Some day I will develop and exchange the investment for the land but in the meantime I'm non-accredited and looking to invest in crowdfunding in the meantime. 

If all you ever want is cashflow, then owning fewer properties with less debt (also known as leveraged) will be ideal. 

Ideally, I'd like to build the 4-plexes in order to live in one and rent the other 3., but as someone with zero experience, would the single family lot be my best bet?

These properties need work and are ideal for flips.

There is an old saying in real estate, "find a great deal and the money will come," but this is ONLY true if you have dug your well before you need the water.My advice to you, if you are serious about syndicating deals, is to first figure out the kind of deals you want to buy and develop an "investment thesis" - what you want to buy, where you want to buy it, and why you think this makes sense.  

My husband and I deal with this on a daily basis.