House Value 330,000.00 Loan 105,000.00 Current Mtg 1,200.00 Rental Income 2,200.00 VA Apt Rent 1,800.00Numbers aren't bad, but here's my dilemma and I need some advice or opinions.

Yep, I got the bad one first and I learned a lot.

Don't feel bad about not being "supported" by the "family member" that is an agent, but not supporting you.

There's been cases when someone bought  dozens of properties subject to, fell behind on all of them because of tenant problems on some of the properties, resulting in dozens of motivated sellers, thinking they solved the problem dumping the problem on a rescuer, losing their homes, and having bad credit to boot.There were extensive discussions on real estate boards regarding the issue: Subject_to_problemsIf you're taking about a 2 year master lease, maybe you're thinking of leasing with option to buy.

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.