It seems risky to continue to defer and eventually be stuck with the taxes on that depreciation when I would sell, I could do a 1031 exchange but will it eventually be recaptured at some point correct?

The police eventually showed up and says my GC has to leave and if he tries to drill the locks out that he will get arrested because it’s “trespassing” and the squatter has “rights” to the property because he has been there for more than 90 days supposedly.

From your deal by deal basis growing your list of investors, banks, lawyers etc naturally you will eventually get to a point where the reg A makes sense. 

I'm currently living in Crown Point Indiana and hope to invest in surrounding Northwest Indiana (Hobart, Merrillville, Portage, Lake Station) and maybe eventually the South West suburbs of Chicago.I'm mostly interested in flipping single family homes and purchasing smaller multi families. 

So, you can ignore the lien, but the eventual price tag will increase by 7.5% per year, meaning the lien will double every 13 years.

Eventually, the affordability gap will close as prices here moderate and hopefully our state government can come up with some insurance crisis solutions.

To your second part, the one nice thing about student renters is that even when you have bad ones, they leave eventually.

I also suspect home prices would initially rise on the first 1-1.5% of cuts, but ultimately fall once we get to the 3-4% range as large  pre-pandemic supply comes back online, compounded by boomer land lords selling realizing the top of the market is in the rear view mirror (at least for them).If you eventually get squeezed on lower rents and valuations as the market normalizes, the ability to BRRR your pandemic era deals will be limited, so how do avoid trapping capital in the deals you already own from this environment? 

Cash flow would eventually come when the rates go down, but equity from day-1 is my kinda game. 

We’re also considering purchasing another LTR near Disney to eventually enjoy with our newborn—a celebration of sorts for future family vacations.