It's like starting a woodworking hobby by trying to build a grand piano.

You don't need to hit a grand slam in your first at bat in order to play the game. 

It would be nice to get some lifestyle lift in this next deal (ie, we use it)3-Long term multi family in Pueblo, Grand junction or similar B market: too hard to manage from afar?

You ask which state you would choose to invest.Well, if you like living in Wisconsin, you could look for a duplex to start with in an area that had rental demand in the path of progress that was affordable to you.If not, I would make the drive over to Michigan and look at a markets like Lansing, Grand Rapids, or Kalamazoo.

My goal is to be financially independent by 30, I would like, passive, around 6 grand a month, enough to be comfortable without a W-2 job.

But $30k-40k is a lot... or is not, in the grand scheme of peace of mind and long term appreciation of a 1/1 condo in San Diego? 

Just reading data sheets will teach you nothing about that area.Unfortunately, I never found a source that isn't some type of shortcut grand summary. 

I have a large construction background, and currently I am a small business owner operating in Grand Rapids, Michigan.

For example, if your payment will be around $2,200 and the tenant’s paying $1,700, ask for a $4–5K credit to bridge the gap until the lease is up.You could also have the seller offer the tenant a cash-for-keys deal before closing — sometimes a few grand up front gets you the vacant unit you need without dragging it out.If you go that route, just make sure your lender’s cool with it.

@Eli Gosnell there is likely some specific forums for each of your questions if you want to dive deeper but in general looking back I think I was so so so afraid of maintenance things and major issues coming up, and the reality is, even with every precaution they will happen and come up, and even the major ones (water line break into a basement) end up not being that big of a deal in the grand scheme of things.