One guru states, generally 90% of his students do NO business whatsoever and about 8% do one deal before quitting, with the remaining 2% doing "okay" to doing "well".

Its a 2-unit property on Airbnb. 

Daniel,Seems you do have a lot, it seems there are a lot of "predictions" to values / costs increasing in there, one thing i saw is that you have loan Interest payments/ cost increasing every year too, if you have a fixed loan those costs will not increase, they will decrease and your Principal payments will increase.

I would definitely take a look on it.

The catch is it has a violation for building garages without permits.

What data do you gather and what tools do you use to optimize this process?

This will hurt the tenant's credit score, it will warn future landlords when they run a credit check, and it will prevent the tenant from qualifying for a personal loan, home loan, etc.

Why would you do a cashout refinance in 5 years? 

I get the gist of this but not completely sure how it works out also would it be smart to use a private money lender for gap funding in order to come with the capital needed to get approved for the fix and flip funding?

Do you want to be involved or mostly hands off.