Fortunately, my predictions were correct and all tenants happily signed a one year lease with the new rent amount. 

Fortunately there are plenty of traditional housing options that are perfect for flipping.Which island are you considering? 

Fortunately there is no loan on that one to deal with.

Fortunately, the challenges of operating in the California or New York real estate market don’t apply nationwide.

I am fortunate enough to have found a job that will pay my school debt or else my funds would have been tied up.

One was fortunate enough to have hooked up with a great contractor a year or so ago for work on other properties he owns in the area (so got pretty much immediate attention), the other I helped find a good contractor but he had to wait until that contractor was available. 

I’ve been fortunate enough to find a mentor who is showing me the ropes and is basically giving me cuts of his deals that I am working for him but we’re going about it as a JV, as it’s allowing me to learn the process of the sale, getting a contract, etc.I am also currently in the process of buying my first home and the loan application is in the process of underwriting.My question is, if I get a contract on a wholesale deal (still working on closing my first deal) and the take that to title, will that affect my loan process on my primary residence?

We pay an annual fee for this and we've never really "used" it since, fortunately, we've never been served legal notice. 

I’m fortunate to live in a country where insurance stupidity is still below apocalyptic levels.

To me that effort is larger than $30/month.I would not do it for a total expected return of $100/month, $200/month, or $300/month either but I realize I am in a fortunate position and not just starting out.