And it's been three weeks since the last bad rainstorm when I had a dipping ceiling.  

We have 3 kids, have lots of bad debt, make less than $100k/yr combined and work WELL over 40 hours a week at our normal jobs.

@Mark DiGioia my bad! 

@Cory Peters Pulling out some equity to purchase another property isn't a bad idea, but it isn't your only option. 

Its tough to start out in this area at this time with the prices around the Medford area, but there are still some opportunities looking a little further out in the areas such as Malden and Everett but it is also not bad to look further towards anything close to public transportation into the city.

Not helpful but if you have bad areas maybe you want to convert rooms over time.As far as windows go - there was a HUD grant out there for window replacement in older homes. 

Now, it seems that the condo was a bad idea because of the HOAs, and we want to get out.

I need a 1031 replacement property badly.  

You’ve gotta take the good with the bad and see the silver lining in everything.

I have seen properties with bad language in the lease and the existing tenant, essentially a train wreck waiting to happen, that i have passed on buying - life is too short to take on known problems.