single family, dueplex, condo, 4 plex .... need help

[Ron Pearson]

Hello, I am new here and this is my first post.  My ultimate goal is a place to live and cash flow investment properties.  I live in an area that is supported heavily by oil and gas so I am quite sure there will be a non trivial market correction in the comming year unless something with oil drasticly changes.  My question is I am able to find decent single family homes in the 280-320k price range but duplexes go up in cost quite a bit to around 400k but it would give us one rental property right away but then we would be paying a larger mortgage for our primary residence rather than having a separate building we could sell off if need be.  The other option is to just buy the single family home and then buy a 4 plex but the 4 plexs I am finding are not super nice and while the market today in anchorage commands rediculus prices for rent even on marginal condition places, will that trend go on forever?  No one wants to be the guy that over paid for a run down property because todays rent prices were good.  A third option is to buy the house and then just buy random condos sprinkled around town, this option would allow me to either buy the units outright so that I dont have any risk of forclosure if there is a vacancy.  Plus there is more supply of condos and nicer condos.

I like the idea of either putting a ton down on an investment or paying cash becuase everyone says "insert bad thing here" will never happen ... until it does and your standing there being forced to take less rent while you have a fat mortgage you are having to subsidize with a regular job which is negitive cash flow.

I have 40k saved now which will go towards the primary residence and then another 120k worth of raw land I can sell (estate just sold some like lots so I am pretty confident I can get at least 120k).  The land is 10 acres but is out in the country, not the middle of no where but pretty far out, but its 10 acres and new roads are being put in and it has natural gas so maybe I could build rentals on it as I go.