Don't even apply for other financing until you have past your loan closing, it's not just a ding on credit, not disclosing anticipated debt can give you a real problem, so give yourself enough time to have discovered your next deal , not in contemplation of creating more debt prior to closing.

I don't have enough of a background to provide you with, but I can tell you are contemplating it for 2 good reasons: 1. vacancy, 2. you have a heart.  

Matter of fact, the house that I'm contemplating buying is the house that I'm renting itself along with 3 other roommates (2 tenants and the landlord himself). 

I am contemplating selling it and trading into a new place closer to where I live to shrink up my span of control.

@Craig Stahl you just answered a question I've been contemplating for the past couple of days!

@Brian SmithI can't tell for sure if you're contemplating doing your first deal or if you've already done it - but the challenge of financing and the 'time lag' was something real that we've dealt with. 

I was contemplating this approach because I am very familiar with the rental property area as many of my friends have lived there and I visited that area many times since I graduated (I still live in that city).I understand it's difficult to analyze a situation given limited info but is there any obvious downside you see in my approach (e.g. need to take out two mortgages?)

I was even contemplating a multifamily in NJ or Staten Island. 

I've contemplated having a partner and have a few people in mind that I could use.

I am contemplating on if I should rent out my entire home.