Even if I'm under market value, I'll ease up the price through the years to catch up, while hopefully not causing a vacancy.If a tenant moves out, then the asking rent gets moved to market value for the new tenant that we find.There could be rules in your city or county that dictate a maximum percentage increase per year.  

Not only was the roof leaking, but there were trash barrel lids under the spot that was leaking, apparently in the hopes of catching the water.My question is how do I handle this? 

So, hire an inspector the first 2-3 times, 5 times maybe, but after that, save your $300-$600 for the repairs and deferred maintenance you'll need to catch up on after you buy the place.

Is there anyway to get the full amount plus the catch up, so 25,000 I believe,  into the 401k and then into the Roth or does all the contributions have to come from my earnings. 

The catch is, the job is located in Saint Louis, MO.

@Andrew K. yes I've heard that many of the roofing companies are still trying to catch up with damaged roofs from September's hurricane.

Like I said, I think the industry is catching up to this and capitalizing on it. 

Our goal, take the house back or sell it at auction, never giving the borrower a chance to catch up on the loan or modify.  

At some point the market for larger lots will catch up in value if ADUs cashflow well in your region.

In that case if they fall behind they may also struggle to catch back up.