I can deduct a cleaning fee from security deposit separate from what one might consider normal wear and tear?

https://www.clevelandohio.gov/city-hall/departments/building...A few properties are still registered, you can check them here: https://aca-prod.accela.com/COC/Default.aspxIs this an intelligent method of getting a rental registration and improving the city?

:Plan 1:Buy a small sub-$250K townhouse in cash, provided the price is right.Take out a line of credit/HELOC/etc. on the townhouse.Buy a second similar property with a large down payment and bank or seller finanancing.Enjoy the cashflow.Repeat when possible.Thoughts: Less tax benefits, but less risk.Plan 2:Buy a small sub-$250K townhouse either all-cash or with a mortgage but as an owner, not as an investor.Live in the property and possibly house hack.Once funds allow, purchase another property.Enjoy the cashflow.Repeat when possible.Thoughts: I udnerstand there are additional tax benefits to this method.

Mainly have scaled through BRRRR method and some flips to acquire multi family.  

Some states let you charge storage fees that eat into security deposit.

The "Chart of Accounts" of the accounting folks creates the categories, such as Rental Income, Security Deposit, Plumbing Expenses, Groundskeeping, etc. 

Quote from @Michael Santeusanio: Do you think experience carries more weight than numbers when securing capital?

Others stick with spreadsheets but update them monthly instead of waiting until tax season.The biggest mistake isn’t the method — it’s falling behind.

So, they have been living in our property that we have to make payments on and have only given us a security deposit and three months of rent for 8 months being in there.

The focus should be on solid systems, dependable plumbing and electrical, safe flooring, working HVAC, secure doors and windows, and items that will withstand long term tenant use.