Of course, the value will likely increase once the hospital and hotel come in, so if you can and want to hold it, I'd look for other ways to generate some revenue from it in the meantime.

Even if you leased it up to 50% occupancy it is generating much more income, so the value is basically what someone is willing to pre-pay now for the work they will eventually have to do to later to get it occupied and operating better. 

Currently financial figures are as follows:Mortgage: $2200HOA: $550Monthly Property Tax: $600Maintenance: $50-100Total Monthly Cost: ~$3400 / month Rental income generates around $1400 a month leaving me with an "effective" monthly payment of $2000.

If it is to generate consistent and reliable cash flow an apartment complex in OKC is a great way to go.

Do laundry really generate income?

As for Milwaukee, it's as diverse as I'm sure many cities are, with room for opportunity and a lot going on externally and internally which is generating a lot of hype.

Selling I don’t really want because my first property is in a great location and it generates great cash flow.

My best advice would be to go to as many meetups or networking events as possible while you're in the generating money phase. 

I have absolutely no idea how the Bay Area market functions, so I'm not at all qualified to answer whether that's predictable.I think it's equally risky to an investor putting up $100,000 on a property that the investor expects will generate $150,000 in profit. 

One thing not mentioned here is I would look big picture and figure out the returns you plan to generate and whether that would make sense for you and other investors to tag team a SF rental....