He told me I can't take any home office deduction (I'm interested in the "simplified one" $5/sf) because I'm not a Real Estate Professional (750 hours spent or half my regular business time).

I was not in Social Security due to being in full time ministry, therefore would not qualify for Medicare at retirement.  

@Paul LaSpina The amount of money it will take you to hire a competent securities attorney and other professionals (CPA, etc) will far surpass your needs (assuming this is just 2-3 people). 

My other prospective tenant is willing to pay a double security deposit (prepaid rent) because his credit is week. 

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

My guess is that you have not been doing regular/quarterly property inspections.

*Provide information about rental rates and other terms and conditions of the rental, as set out in a schedule provided by the owner, and*Accept deposits, fees for credit checks, and other administrative duties, security deposits, and rent*Provide preprinted rental applications and respond to applicants’ inquiries about the application*Show rental units to prospective tenantsAs you can see, a non-licensed, non-resident manager is limited to performing rather routine tasks that don’t call for initiative or decision making.For instance, this manager would not be qualified to negotiate a lease (4), deal with late rents or other violations of the rental agreement or lease (5), or appear in court on your behalf (6).(1) My property manager does NOT live on any of the owners properties.(2) My property manager is unlicensed.(3) My property manager supervises 10 different properties.(4) My property manager has negotiated leases for 12 years without a license.(5) My property manager has dealt with late rents and violations.(6) Unknown

Any person, partnership, association, corporation, entity, or their regular employees, who as owner or lessor perform any of the acts enumerated in §§ 54.1-2100 and 54.1-2101 with reference to property owned or leased by them, where the acts are performed in the regular course of or incident to the management of the property and the investment therein."

As an example they add up the security deposit to the rent amount and the statement says they paid it to you, but the reality is that they hold it.So yeah their spreadsheet is quite useless and you need to build your own.Airbnb UI is better in many regards but they only pay you when the guest is in and keep the money between the reservation date and checkin date.

It's also a backwards experience from regular jobs, in that the broker or manager doesn't really interview you, but share with you all the things they can do for you in the brokerage to make you a great agent, which is all total BS.