Now here's a 7-unit multi-family that I found online and decided to test out my analysis skills.

However, my expenses based on the expenses I am seriously overshooting the 50% test ($1450 for 50% test vs $2075 estimated expenses). 

@Provi Hall - Il has reciprocity with FL so you just need to pass the test and find a sponsoring broker - no need to go through the schooling 

Maybe planning a sabbatical is an option to test the W2 retirement waters?

I'm hoping there's a tried-and-tested, standard way to handle this that we can follow (e.g. we charge the fourth a management fee or something simple like that).

We also did some initial market test and received positive feedback.We tested the waters with our local bank and got the response that they don’t lend on speculative projects.

Have to watch out on 5 year loans as mid-process to fund the loan some lenders will stress test the property as part of an appraisal and then require a larger down payment.

I've tested this by calling at different intervals to mention to them that I'm concerned about how certain properties are showing up (or not showing up) on the search map in our area, and to inquire about booking dropoffs (at strategic times).

You certainly have time to experiment and test out the waters with real estate.

Although I have had an investment since 2013,  I haven't been tested.