@Christian Wathne Didn't mean to imply that the properties would be in WA or CA.

What typically happens in rent controlled areas is those restrictions end up restricting the supply of available rental housing, which ironically drives market rents up even further ... not to imply that it is illegal, but it is kind of a kin to outlawing drugs doesn't stop drugs from being bought or sold, but it does drive the market value of those drugs up.

My goal soon is to acquire a mentor/trainer and get started on real estate investing.It's nice to be apart of a growing community!

Hi my name is John Te, 27, personal trainer.

There is a lot more than structural/electrical work that the property needs like appliances, many cosmetics and two furnaces are ~10 yrs old.The property could bring in 4300-5000 gross rent (500-600 per room is market) so the value is there but when I add up the 25% down, cosmetics updates, appliances, furnaces, and *basic structural work totaling at least 25k* I lose interest.Initially the sellers agent implied they would be willing to do the work (the agent is the owners daughter and he's apparently a big contractor).

If you can't find anything better (assuming you looked long and hard), the market could be factoring a shortage in housing opportunities and implied appreciation.  

As implied above, the co-borrower is going to impact how the loan is structured, but if they are a non-veteran, the VA will only guarantee the veteran's portion of the loan.

As @Ralph R. indicate #2 is likely to result in negative cash flow.You did not indicate the worth of the property but I am assuming $200K profit with only 6 years left on the mortgage implies low leverage). 

Did you mean to imply that you had moved from active real estate brokering and are now teaching full time?

Initial numbers will only tell you a small portion of the story.Or maybe it is a great deal, based on NOI, only your post implies emotion, and you are infact capable of walking on the deal.