I don't plan to remain on the West Coast in perpetuity...we're figuring on 5-8 years max.

@Travis Brizendine A very good friend of mine just showed me how to legally defer my taxes into perpetuity.

The home is the stereotype for an easy fix/flip: 3/2, hardwoods, brick, one level, large lot, across from an elementary school, new roof, etc.. 

I have good relationships with my vendors and was able to get it for only 82 cents/sf.The sweat I put in to the tasks that I was able to handle myself, allowed me to invest the saved capital into the mechanics and bones of the house (foundation, new roof, new plumbing, HVAC, etc.) and allowed me to get slightly nicer finishes than I would have put into any other investment property I wasn't intending on living in.The goal with this property was longevity, since I will be holding onto it in perpetuity. 

That is true, but then again depending on how approachable and kind you are to the person when speaking to them it could change their previous assumptions on stereotyping real estate investors.Basically, what’s the worst that could happen?

I could possibly buy a couple buy & holds from a wholesaler, make my 30% back equity alone (which I don't plan on selling) and reaping the monthly benefits now into perpetuity while I'm young. 

He also made some very poor investments (stereotypical bad Dr moves) such as a spec-home flop, land purchases out of state and scammed by a con-artist advisor for about a $1M (guy went to jail, not sure about $$ recovery).

@Jaysen Medhurst this is very much a stereotypical "Main Street America" location. 

I highly doubt your friend would be amenable to a blanket perpetual easement on the property for a billboard, but I have seen it happen.

I'm not opposed to efficient urban housing, I just don't want to get rich perpetuating a slum.