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

@Brice Alef-Torrisi putting each property in its own LLC is usually overkill.Getting a bank account for each LLC is typically something you need to do to avoid "piercing of the LLC corporate veil" (actually depends on tax selection you made for LLC), but is also overkill.You haven't indicated how you are holding the deed for the latest property.If in your name or same LLC, you don't need a separate bank account.If in separate LLC, you can create a Master LLC, have each property LLC hire the Master LLC to manage their affairs, and just get a bank account for Master LLC.This is an opinion, not advice, so lookup CPA Frank Alcini in Troy for expert advice.

Great hosts will be good neighbors, will contribute to local tourism and will pay their taxes and permit fees* A major area to improve on the proposal is the 1 hour time-limit for resolving complaints.

Property taxes are also insane.

This is the BEST $100 you will ever spend, and if you listen to Amanda Han's tax book, you'll know it's also likely a business expense for you to write off :) https://biggerpockets.supercast.com/My perfect way to learn from the BP books is to listen to the audio book through the subscription above, then books that really stand out to me I go old school and get the physical copy so that I can re-read it, take notes in the margins, and put post it notes so key points are easier for me to re-reference in the future.

No management costs as it would be self managed, and estimated property taxes by the average of the past few years.

These are features like online renter payments, tenant portal (for payments and work orders), help keeping track of work orders, tax reporting features, and accounting functionality.

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

So obviously being in foreclosure, absentee owner, tax lien or any of such "distress" doesn't make you motivated.So what you need to ask yourself is "how do these software determine who or what is a motivated seller right?

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