You are very clearly leveling up your game quickly!

@Robert Spiegel Great question, and it’s always a balancing act when dealing with long-term tenants who’ve been fantastic overall.Based on my experience managing over 1,200 rental homes in North Texas, including areas like Dallas, Fort Worth, Plano, and Frisco, here’s how I would approach this:Cleaning Charge: While $540 may feel steep, it can vary depending on the size of the property and local market rates.

Retain proof of that notice and make sure you include the new tenants right forms required by the city now.

It seems like it "should be" good with some good features for the price (specifically I'm looking for an easy way to sync pricing across platforms including my website).  

I am using the BRRRR Calculator and was wondering if Homeowners Insurance estimate was included somewhere or if I had to manually enter it somewhere? 

Include a sweet outdoor area maybe with a pergola, jacuzzi feature.

@Jonathan B.Assuming you pass the "material participation" test for 2023 and did not use the property yourself (or used very little), you should be able to treat it as an STR for 2023, including bonus depreciation.  

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases: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+ (roughly 5% probability of default), 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 (around 10% probability of default), 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, this will be brutal for Non-EU countries including the United States. 

There are plenty of older homes on the market that do not have closets.You need 2 egresses (including 1 that goes outside) such as a door or window, size about 70sqft (local codes may differ), ceilings at least 7ft high, and it cannot be a walk-through passage.As always, your local codes may be different.