You can also perform  a 1031 exchange on the other half when you sell and make that gain tax deferred.You're jumping in the deep end but asking the right questions.  

I think the crux of the matter, however, is the fact that if I'm break-even on paper before vacancy and repairs (and management fee, which I'd seek to avoid at least in large part), I might be deep in the red every year (but probably not more than principal accretion).  

The roots can be deceivingly deep. 

It seems like it would be easy for a tenant to dig themselves into too deep a hole.  

My acquisitions only happen at the deep end of that discounted space. 

Yeah, it isn't easy to find the deep discounts.

With that being said, take a deep breath, carry on, just learn as much as you can about the process, and put together a great team of professionals that will look out for you 😊  👌

It needs a complete renovation.I would like to get the property at a deep discount and help the seller as well, but I don't see how I could get it as a discount and get him his 15k.

@Carly Franklin  I think Hands down the best meetup in Portland Is RareBird.. they hold monthly meetings.. they bring in great speakers ( like me  LOL)  but in all seriousness its run by two guys that have very deep knowledge of this area and both very sharp.. they don't pitch and the crowd is great you will meet all sorts of like minded folks.There would be one thing I would do in Columbia county and that is TIMBER...

Basically it was a floating university that laid the travel bug deep in my soul.