Any advice or what you wish you guys did ahead of time?

A place that had some really bad flooding as of late comes to mind when trying to market rapidly built, sturdy homes

Seller wants buyers to purchase the property in "as is, where is" condition, even though the properties aren't in bad shape...just a little outdated.

Local Boston guy that does all of my rentals.

As an aside, the tenant has also been several days late to pay rent for the last few months, but I am having a hard time faulting them due to the hardship from the increased utility bills.I'm not a shady guy and I want to make this right, I just don't know the best way to do so.

We can also pay this guy off for a tiny fraction of that price to get this done quickly. 

I'm bad about learning and not doing.I've also seen strategies where people buy downtrodden homes, fix them up, refinance, and then take out a loan on the appreciation, and buy another home.  

Not a bad idea - i'll do some research and we should talk. 

I've had a couple good experiences, but mostly bad.

Too bad I didn't see this until just now - @Robin Maza and I were at BREIA last night as well.