You sell after 12 months and take no depreciation expense in the first year.  

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

My plan is to take the next six months to try and learn as much as possible about multifamily real estate, while also saving up money to be able to start a career in brokerage.

It sure does take a village Adam!

Now I can see some builders having an issue with comps.. but other than that its crazy to take these funds as income and then pay tax and plow it right back in.. 

You will take care of repairs under say $200 or $300.

The bad is long gone in the rear view mirror so now, that motivation of making the bad go away, has gone away. 

From there we identify properties that could have some potential and if you are interesting in diving deeper, 1) we do a thorough video walkthrough to give you a realistic look of the property, 2) we give a ballpark estimate of rehab costs (we do 40 a year with our GCs o we will get pretty close), 3) we talk through market rent with our property management team, ARV, and potential highest and best use.Ideally you find great investor agents who know their market really well and have a network of resources to provide you with enough confidence to take reasonable action. 

I usually assume it will take 60-days to lease up.

If I am going to take time to prepare it, then I am going to want some kind of commitment from you to stick with me.