My roommate was interested in financial freedom so figured it wouldnt hurt to go with him and see if i can gain something out of it. 

I've been trying to  go through the buyers agents first not wanting to see someone's work for free and honestly this is the first bit of resistance I've felt outside of having to wait several days for showings.

@Michael PlanteI personally believe that while being a landlord is not what you want to do, it is the best method to go about doing business, even if you continue buying properties cash.I would have told my father to be a landlord.

That frees you up to go anywhere you want, and allows you the time to start your new business. 

I don't want it to sit vacant forever, but I also don't want to go through this nightmare again...

Due to the deferring goals of my business partner and future wife, it wouldn't be wise for all 3 of us to go into deals together.

I have been looking in other places, but being unfamiliar with them, unable to go see them quickly, makes it a little tough as I'm a hands on type of person.

I know zillow is not the place to go to for estimates I just wanted to put it out there.  

You are probably going to have to go with a Commercial lender who can think a little outside the box.  

Hi everyone, I wanted to throw out a question and get some ideas/feedback back from you guys.Trying to soak up as much information as possible before I make my first purchase If you had to start from the beginning,  a...