This will likely mean that I will have to take into consideration mortgage insurance on both properties eating into my cash flow until the proper LTV can be met.

Don't eat yellow snow :)

This is still a new purchase and the deferred maintenance will eat up any cash flow for some time.

The ice melt chemicals they use up here in MA and NH just eat right through them (I'm sure it's the same in other parts of the country that have snow).

I’d love to make the move now but if I end up paying a ton of fees that eat into my rental income or simply can’t do it that would suck.

Hey @Zac CelliAt that price point for a single-family home your cash flow is going tobe low. 180k will be an A class property and it just eats into returns.

I am sorry to hear about Aunt Tilly, but I still need to be compensated for lost rent and since I didn't kill her there's really no reason to expect me to "eat the loss."4) I include several "forfeiture statements" in my holding FEE agreement. 

I know what you mean by BP inspiration, boy I’m eating and sleeping real estate since joining!

Oh and eat some of the world's best chili to. 

Examples: Instead of getting general admission tickets to a concert, you'll be able to buy back-stage access and meet the artistInstead of going out to your local dollar-beer night on Thursdays, you could afford to go out and get bottle service (if that's your thing) Instead of going to Chipotle for lunch religiously, you could take all of your close friends to a more expensive restaurant on you- without having to think about itInstead of backpacking across Europe and eating ramen the whole time, you'll be able to travel comfortably and experience whatever intrigues you, passing up on nothing (again, if that's your thing)These are just quick examples off of the top of my head, as they are the things that I myself end up 'passing' on most frequently.