Wanted to know if landscaping is a tax deductable expense in general and if it differs when one unit is owner occupied.

The Big plus is the tax deductions they will be able to take as well!!! 

It would/could be only 15% capital gains tax and yes you could/would deduct all selling costs including commissions and transfer taxes.

There are some zip codes where you can indeed get above market rent with S8 (even after deducting utility allowance), but some where they are lower.

Nate @Nate Marroquin   You can use the income from your tax returns on the current rental adding back your paper loss (depreciation) and add back the mortgage interest, property taxes, home owners insurance deductions on your tax returns. 

This figure includes allowances for heat, electric and any other utility that the tenat is required to pay and this is deducted from the FMR. 

Before the income subject to UBIT is calculated you can depreciate and deduct expenses and losses on that portion of the income so generally it's not as bad as people think. 

The major pieces of information you are missing include NOI which includes deducting all of your operating expenses from your gross rents sans debt service, market dynamics (what are vacancy rates and asking rents like in the market the building is located in?)

Proceeds to segregated account to be disbursed ONLY on rental property improvements and expenses to preserve the deductibility of interest on your Schedule E.

You could also do a cost seg on the $500K sale which depending on what the dirt is worth you can take a large deduction year one of renting it.