My biggest fear with Anchorage is that Alaska in general is so heavily based on oil prices.

I want to start wholesaling in Wisconsin and I was gunnho about it but now im fearing its illegal should i tell the seller my intent and assign the contract or should I try to get transitional funding somehow and purchase the property and flip it quickly. 

Once you do the research, you might find it will take away the fear factor of owning an apartment so you can truly determine if it resonate with your goals. 

@Sarah Fears- are these disney rental props listed on mls?

One of the big fears going into this profession is running out of savings. 

"Be Fearful When Others Are Greed and Greedy When Others are Fearful" - Wareren BuffettPoint is, just because nobody is buying now doesn't mean they wont in the future.  

LLCs and land trusts can slow down lawyers from taking smaller cases because they fear they won't get paid if there is no money behind the LLC, landtrust, ect. 

I don't go to work each day and fear losing my job.

You indicated that this is a Self Directed plan and then you indicate your accountant said you would need to replace the funds in 60 days.These two things don't really go together and I fear your accountant is not well versed in self directed retirement plan investing. 

My first property was a condo and due to issues with the HOA and my persistent fear of special assessments, I sold it.