However, there is also a realistic possibility that waiting can trigger another factor that works against you.

I think the sale triggers a change from passive to active and it can be used to either lower basis or offset capital gains/depreciation recapture and if any is left your ordinary income.  

I’ve been doing my due diligence for over a year now and I’ve finally come to the point where I need to pull the trigger.

Most investors are doing LLCs from my experience... but that doesnt mean you have to. there are some liability protections with LLC, along with a little anonymity if set up right. but also some added costs. one suggestion here is just whatever you decide, stick to it. some counties will see a transfer between personal/ LLC or vice a versa as a 'sale' and trigger property tax reassessment.  

If I were you I would reach out to the mortgage holder to get permission to transfer the property to the LLC without triggering the clause.

The fha 100 mile rule will be triggered whenever you try to vacate your current primary and also trying to use the rental income to qualify.However, this 100 mile rule can be exempted for the following rulesRelocationIncrease in family sizeVacating a joint owned propertyNon-occupying co-borrowerIf you are not trying to use FHA on your 2nd househack, you can use conventional and the rules that I mentioned above will not be a concern.

I think the biggest thing I learned from this is not to pull the trigger too fast on buying a house.

This is throwing money away for the most part as they will charge for their time if they have a lot of business.It is more common to have a GC walk a property before you go under contract, but the good ones will stop answering your calls if you never pull the trigger.

Talking about a potential conflict of interest and credibility issues, I actually saw a post you made 6 months ago (https://www.biggerpockets.com/...) where you wrote: "I know that there are many more people I've helped who haven't pulled the trigger even though they wanted to.

@Ven Reddy, I'm curious if you pulled the trigger on this.