We definitely are going to pull the trigger this year and do it, time to learn while on the job per se.

I'm not sure if it's possible in my situation, because I know that you need to be self employed for at least 2 years to be able to get a loan, and I don't know if the lender will take into the consideration the money that I have earned before turning 18.

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 house hack, you can use conventional and the rules that I mentioned above will not be a concern.

My wife and I came very close to pulling the trigger out of state. 

I've been burned a couple times early on, but the type of personality that operates with no consideration of anyone else but themselves is easy to spot with a little experience.  

I would recommend buying new properties in single purpose LLCs - if you transfer them now you would trigger a transfer tax event unless you put them into a land trust. 

Taxes are also always going to be a consideration, and this is an assessment year, so you should account for them going up more than usual in your projections.  

If it's just repairs, then.... again the same considerations but, be sure they warranty the repairs too!

Here are some considerations to help you make an informed choice:Risk Tolerance: BRRRR projects frequently include more risk, particularly in the event that the refinancing fails to recover all of your money.

I am taking in school districts and overall convenience into consideration but don't know what else.