Hey Fabienne,I am a builder from Suffolk County but do most of my work in Nassau County (north shore). 

Depending on how flexible you are, you could get a temporary housing situation if the August deadline comes upon you and your wife before you have the multi-family purchase set.

I know these are all red flags and I should have done my homework but honestly I just needed a temporary manager until I return to the area.

Not sure exactly what all they were doing, but it has some temporary hand rails, and they said they had cleaned a bunch of junk out of it.

At this point you REALLY NEED to assess your current tenant and decide if this is a temporary blip in the road or if they are not going to last long term with a more systemic and continuous problem. 

Now owns a rather successful chain of pawn shops.Client owns these two properties:River Forest: $600-$800k equity (Owes $400k)Oak Shore: At least $1 mil equity (Owes $175k, worth minimum 1.3mil up to 2.3 mil, I haven’t looked at the property, it was a distressed purchase)Looking for $800k hard money to close on a 43 unit apartment complex.

Find a deal and then find your mentor- even if they are just temporary find someone you look up to and someone willing to walk with you during your first steps into this new path you have chosen.

If you have experience with waterfront property, esp in this neck of the woods, I'd be grateful for your thoughts.Basics are that it is a ~950 square foot home / cabin near Dyckesville, WI, about 1 mile north of Bay Shore Park.  

It could create a temporary softness that could create a buying opportunity.  

Plus, there's a niche to be filled by offering the smaller homes - boyfriend/girlfriend, recently engaged, temporary out of town workers, and just plain single people.The 2/1s tend to have more turn over than a 3/2, but it's a niche that many investors overlook, and still a good segment of the housing market.If the numbers work on a 2/1, I would continue your due diligence and proceed if everything makes sense.