Now a historical area on the other hand, with restrictions... this makes me look at what I will have to do and the extra steps I would have to take to do it. 

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

However, from the little I know so far about QuickBooks, it just doesn’t seem that it’ll help with maintaining historical data.

Historically appreciation is where the money is.  

When bisecting the historical comps you can see what trend is rising, falling, crested and descending or taking off. because when you flip, your a housing fortune teller.

Market is right now at a historic low, so its time to invest. 

The MLS by it's very nature is historical, not forward looking.

Housing is at a historically bad time to buy right now because the combo of rates and high home values one of the two needs to correct and i'd recommend waiting that out.

The area is a Historic District and very walkable, which tourists love. 

I have yet to see a counterexample. https://www.foxnews.com/opinion/bidens-rent-control-plan-onl...What continues to amaze me is how dense people are when they are not willing to look at historical examples of what happens when bureaucrats and politicians intervene and therefore artificially change market dynamics.