How would this be accounted for for general accounting and taxes?  

An other advantage of paying with credit card may be that you will not have to send the provider a 1098 tax form (only an issue if the total yearly amount is over $800). 

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

Dig deep into tax strategy, tax efficiency, etc  Learn about estate planning. 

We're right next to CA but get the benefits of no state income tax, 4th lowest property taxes, much more friendly landlord/tenant laws, no serious weather, proximity to Lake Tahoe, stable job growth/population growth, etc. 

So, when Trump changes to no tax on tips I feel inclined to change my rental income structure.50% reduction in rent.Previous 50% made up from a mandatory nontaxable tip. 

There may be tax implications to that maneuver, so check with a CPA.

Additionally, most servicers will provide the tax documents needed at end of year (1099-INT, 1098-INT) and can also issue notices of NSF, late payments and support delinquency /default.

Property taxes are 2% instead of 1% for landlords as a general rule (some districts may  be slightly higher). 

For several reasons (property taxes, politics), I would prefer to begin real estate investing somewhere other than locally.