Even though your condo may see additional appreciation, you can't eat equity.

Plus, you're incurring additional expenses that eat into whatever equity you do build up in your 2-3 years.Fair warning, the rest of this may seem like a bit of a downer but having just spent 5 years stationed in San Diego and, after a lot of research, deciding to rent while there and invest in other markets, I think it's worth presenting for you to consider. 

(the personal one went through fine, just not the business one, income isn't an issue) Or do I suck it up and just eat the lost money?

Large Multifamily can easily afford a property management company without eating too much into the profit.  

Will likely eat up some time but at least no add'l cost. 

I am fine eating a few thousand up front to benefit in the long run, but will still need to sell my house for a profit (let's ignore whether or not I can get X dollars above what I paid just 6 months ago).

I can tell you this, it won't take long to eat up $44k in attorney fees.

But you've got to make sure that the acquisition price of the land will eat up your reinvestment requirements from the sale. 

For me the numbers on This return would fit more favorable with white collar cities because I would be able to landlord on autopilot or less hassle free than blue collar towns in rural areas where if one loses a tenant it may be months of vacancy which will eat up profits in no time.

In this case, the chicken came first.And you're right about how a good full time agent will eat your lunch, but hopefully within the bounds of ethics and good taste.As a full time (and then some) agent, I'll remind sellers that most part timers tend to treat this profession as a hobby, hoping that while they hold down another full time job, that they'll trip over a couple of deals each year.