I also agree that RE appreciation is unlikely to match the last dozen years, but you never know.Where I am unsure we agree is that paying $450k to improve the cash flow ~$3k (your numbers but I expect my delta wold be similar meaning both my cash flow estimates would be worse than yours but both would be worse by the same amount not affecting the difference) makes sense especially if the cost of having the extra $450k is only 6% rate which is historically simple to beat via numerous investment options and hopefully no one is investing in RE for an expected of 6%.  

With software, it's only as powerful as its user so some clients overcomplicate things and spend most of their time trying to "fix Quickbooks".The most successful and quick clients keep it simple or keep it to their comprehensive level. 

At its most simple we’re separating the appreciation/capital buildup benefit from the cash flow benefit.  

Keep it simple - sell the property and let each sibling do what it is that they want.If you keep it and do a refinance(to pay for the bills)Who will be on the loan, will it impact everyoen's DTI?

Do you still recommend using a real estate CPA or is their tax professionals that specialize in the more simple investor situations like mine?

Finds (1) half of what plaintiffs told him is incorrect or untrue; the potential defendant has filed all the correct paperwork for Reg D and hence has “statutory” protection against almost all but fraud; unlike what the plaintiffs believe and told the attorney the risks WERE disclosed to them, NO specific return was promised them; and the defendants have not stopped communications; they merely grew tired of the 82 daily phone calls asking, accusing, and raging by the same three plaintiffs.  

Brown: I use https://www.bestwyomingregisteredagent.com/Very simple, 100% online, they are responsive if you need help.

What is a good system to create around standardizing rent increases where applicable / best way to communicate it to the tenants? 

Get a stable income, job and start with going the simple route.

New construction, townhome style or even small simple house style - coupled with nice neighborhood amenities, and in a good school zone