Remove,HOWEVER,If you can turn an eyesore into a feature it would be awesome.You could plant a bunch of climbing roses and cever that entire thing in bulging flowers of all colors.It would be very beautiful, and functional.The smartest thing to do however is to remove it simply because most likely the people that will buy your hose won't need it...

Resolution occurs much faster then 'I'll sue you'.Good luckCarol

Currently the property pays $3300 for lawn care in the short Wisconsin summer, while not totally unreasonable I was thinking for half that amount I could purchase a decent lawn tractor for the property and do the mowing once a week myself to save quite a bit.Then the idea of either reducing rent in exchange for one of the tenants using the tractor once a week to mow the lawn occurred to me. 

Do you "trust" that during the 5 other remodels that occured over the last 100 years that everything was done well(ish)?  

Once you have multiple properties, you can relax these guidelines a little based on the likelihood of major repairs occurring on more than one property at the same time.....but having said that, trust me when it rains it pours and you should at least have a back up line of credit to cover you in the worst case scenario. 

It didn't occur to me that they would tear the foundations out all willy nilly. 

It hadn't occurred to me to lubricate them until I was typing my initial post. 

Although, I have yet to see any actual development occur just yet.

The next crash will likely happen in car lending and developing country stocks and not housing.The next time we see a sizeable price drop 1 of 3 things will likely occur:1) Prices will drop but they will be higher then they currently are.2) Price will drop and investors (big and small) will flood the market and buy up the excess inventory quickly stabilizing the market.3) Interest rates will spike caused by either an increase in inflation and/or defaults from over leveraged developed economies.

You get into a better neighborhood (a place you would live -- I think its incredibly important to invest where you would choose to live, or could live in if needed) and get 24/7 hands on training of a property (versus showing up after the problem has occurred, e.g. a roof leak, crime, etc.), and STILL make your numbers on cash flow.I never encourage anyone to pump their brakes -- if the numbers work and it looks good, ACT -- but for someone in your situation, I think you would be better served taking a househack approach versus buying a mediocre property in a bad neighborhood, and hoping a lot of things go right.Good luck young man -- I only bring up the above as a Devil's Advocate.