I am now looking at multiple MFs but the moment I add my forecast of tax increase (new market value, new assessed value and increased tax calculated from the county calculator), the deal becomes worthless or is at least not in the range I am looking at.

Even in our Toronto & Canadian markets there has been 3 major declines over the last 20 years ranging from 10-28%. 

Hello Brandon,Thank you,I agree with you, it's good to think wide.

Within that price range I would guess that you would probably be looking closer to a Jacksonville type area.

I did a quick mockup of some curb appeal, but I think it's over kill for the neighborhood.It is a "Cute" house on what looks like a nice wide lot, or an empty lot next door (that looks like a jungle of mosquitoes and snakes).A little curb appeal goes a long way on some of these lower end homes, but the neighborhoods tend to be "Worn" and it not worth it. 

My real estate agent basically telling me that at that price range anything I find is going to be very distressed and I need to come in with cash reserves to do a lot of rehab.

Or, are you saying any local lender versus a nation-wide lender? 

I think most of those properties are going to be in the 200-300 range.  

The new boat payment would fall somewhere in the $400-$500/month range, bumping me to around 35%. 

I could probably find a cheaper area but duplexes where I'm looking are in the $150-$200k price range and it's been a steady market for a very long time.