For instance, here in Chicago most people house hack either a triplex or a duplex with an illegal garden so they can use FHA loans without triggering self sufficiency.

Each firm will be different.Some will do hourly consulting for anyone and everyone.My firm doesn't provide consulting services unless we also handle the compliance side. 

You may wish to confirm that the new 401k provider will handle the ongoing compliance support such as any required 5500 filing (e.g. 5500-EZ for a one-participant plan with assets in excess of $250,000), any required tax reporting (e.g. 1099-r in the event of a distribution or in-plan Roth conversion), mandatory plan updates and amendments, etc.4.

You'll also need some kind of 24-hour coverage for emergency maintenance, legal and accounting support, and compliance (in most states, you have to be real estate broker - which makes you subject to State audits of your escrow accounts, etc -  to manage for other people).If you prefer to focus instead on building your real estate portfolio, or other things, then you'll eventually need to hire a third party property management company; You may be able to self manage 15 doors but what happens when you get to 50, 75, 100 doors? 

But it takes a high level of commitment to pull the trigger on a less than perfect deal.

Even changing employers within the same industry (nursing/ teaching/ sales etc) will trigger this.

I think with the VA, if I transferred it to an LLC it could potentially trigger some sort of due on sale clause since it's owner occupied, but I'm not certain.

Hey BP community, I'm at a stage in my learning process where I am ready to pull the trigger on my first investment property, pending current economic uncertainties but that is a post I've seen covered plenty already so we wont get into that! 

Buying a property with a loan, then transferring it to an LLC, is not recommended since it is a violation of the loan terms and can trigger a repayment of the loan (even if you didn't sell the house).For depreciation, look into the Real Estate Professional tax rules. 

@Anthony Robinson It can seem time consuming and you’ll want to just pull the trigger, but based on my mistakes - don’t.