A complex trust is generally taxed in the same manner as an individual. Thus, most items that would be considered as a non-deductible, personal expense had an individual paid it, would be treated the same for trust taxation purposes. Just because a trust pays the expense does not make it a deductible item.
Their are deductions allowable to individuals but not to trusts and estates. Unfortunately, medical expenses are one of those. Since the medical expenses do not relate to the trust entity, they may not be deducted. However, they can be passed through to the beneficiary of the trust and deducted on that persons return.
The other items you mentioned would be deemed either as personal expenses (i.e. non-deductible) or capital expenditures (i.e. included into the cost basis of the property) if they result in a significant imp[rovement or lengthen the property's life. If the property is involved in a business activity, then the trust may depreciate the assets and take a depreciation deduction.
Trust taxation can be very complex, especially when a complex trust (i.e. not required to distribute all income earned) is involved. A trust also has special deductions and exemption amounts that are different from individual taxation. I recommend you engage a competent CPA or tax preparer to help you meet the compliance requirements.
Because it is impossible for me to identify and consider ALL the relevant facts, this advice is not intended or written to be used for the purpose of avoiding penalties, and cannot be used for that purpose.