People who are really rich do not do the day to day maintenance or supervising.  

This is due to lack of supervision from the builder to their subcontractors.

. #2 is not going to know how to do this properly, so unless OP has accounting experience and can basically supervise/tell the bookkeeper how to do the job, then #2 likely won't work. $20 an hour will get you someone who knows QB software and can input transactions, but likely not someone that can design and maintain your books at a quality level.Source: I'm an auditor.

My daughter lives in Houston and I am exploring that rental market a little.What you are describing sounds like a halfway house, in which people who are returning to the mainstream from prison, or are recovering from addiction and learning to live an abstinent life under supervision (and daily testing).

Bodily injury or property damage for which the tenant is legally liable would include 1) negligent care or supervision of an animal that bites a third party.

As a property manager, I supervised and maintained the ongoing upkeep of 2 residential units and 7 commercial properties.

In 1973, the Accounting Principles Board was replaced by the Financial Accounting Standards Board (FASB) under the supervision of the Financial Accounting Foundation with the Financial Accounting Standards Advisory Council serving to advise and provide input on the accounting standards.[5] Other organizations involved in determining United States accounting standards include the Governmental Accounting Standards Board (GASB), formed in 1984, and the Public Company Accounting Oversight Board (PCAOB).

Also, you have to have a non-profit set up as a program that can provide that 24 hour care/supervision.

There's limited crew managers, so it seemed like the folks working at each site weren't being supervised directly, so I did get a sense of some 'slacking'/slowness here and there.  

I have been working the tax sale market now for many years and have done well - I work a program called "Tax Sale Poaching" - I don't care much for competition - so I poach tax sales owners where the certificate has been sold or advertised for tax lien sale - I take the time to track them down - when I find them I offer them several proposals - I'll buy their property -Or control their property -Offer to auction their propertyDo a partnership deal with them - (called hybrid auction sale)Loan them money to pay the back taxes - secured with options or pay-back datesTake an option to purchase the property with a buy back agreementConsult with them - let them know their rights and optionsManage the property - rent it - share in the incomeBe a broker's broker for them ( Broker's Broker selects and supervise the best most qualified agent to list the property for owners. - This is best for the seller since the Broker's Broker understands the culture of real estate agents, can interview them and determine their success rate in working on certain properties and with clients and their motivation and can questions them in terms understood by agent and Broker's Broker --- Sellers should not risk listing their property with a new agent or an old agent doing all the convenient and unprofessional ways from the past.There lots of ways to make money with tax sale situations - glad to help - hope this gave you some ideas -"Real estate investors ----- Be different - be bold - go where others don't - talk with sellers daily - profit from your games, get out of the line of conventional learning and keep it simple."