I'm a Realtor here in Chattanooga and work with investors and house hackers all the time, and the biggest mistake I see is them waiting for the perfect deal.There will definitely never be a perfect deal and issues will almost always come up in some form or another, but as long as you do your due diligence and make sure you have the proper amount of reserves in place, you will be fine!! 

Hi Vicki@Gene Hacker spends a lot of time out in Ridgecrest.  

Long Island house hacker here :-) I'd say - it's not only doable, it's also tough to live here without doing it!

If a multi seller has two offers, one from a FHA house hacker and one from an investor, they usually go with the investor because it'll be less headache (investors care a lot less how it looks) and no FHA loan issues.Out of the last 20 house hacks we've closed, only two have been multis.

How have SFH hackers navigated regulations regarding rooming houses and/or boarding houses?

Not being able to find tenants is one of the biggest beginning house hackers have when they first get started.

We personally love 5% conventional :) They are a house hackers friend!

Things like, "Does an LLC make zero sense for a House-Hacker" and why I think trading stocks is silly, but active investing in RE is wise. 

I put together a spreadsheet here to help potential house hackers quickly analyze whether or not a property qualifies.

Partly because you're competing with retail buyer/hackers (and they can afford to pay more because they're living there) and partly because there's a lot of competition from other investors looking to make the jump from SFR.