Whether something is by the job or by the hour would depend on the nature of the repair.

I would always have some type of reserves from day in the bank account.

These add to your balance sheet net worth and is recouped upon divestment of the property.Things you need to subtract from cashflow to get profit:- Accrual for capital expenditures and maintenance (sometimes referred to as reserve)- Accrual for future vacancy- Depreciation if you are accounting for taxation purposes

have enough money put away in reserves, when it rains it will pour, well at least for me

Then, after doing some math, I figured out that many of these properties would be extremely difficult to maintain a steady cashflow from and the looming risk of natural disaster was, well, looming.

Therefore, treatment will mirror your own personal residence (i.e. most expenses will be personal in nature and non-deductible).Any rent she does pay you is taxable in full with no deductions to offset.Then you contend with the gift tax issues.Generally not a good idea to rent to family, but if you do, make sure the rents are fair market. 

Due to the nature of the work it was expected and the guys didn't flinch at all.

It's natural to want to shift the responsibility for those expenses on to the tenant as they slice your profit margin for the year down to nothing and start to hack into the bone for a loss.And this one big reason is why self-sufficient handymen typically do well in SFR, especially the high-maintenance lower categories, while others do not.

I have seen it done with 12-24 months worth of commission history, If there are positive contributing factors like large reserves, and good credit scores.  

In conditions such as those we face today, fulfilling redemption requests would require us to either substantially deplete vital cash reserves, or, even worse, potentially sell assets into a down market, likely at a price far below actual value.