I run an air BnB out of my home in Southern Vt And I own 2 condos at Mt Snow. 

Air BNB allowed.

I have heard from others that you should learn and research tax if possible for your first property rather than hire CPA right off the bat as it should be less complex from strategy.

Just hire an electrician, hire a plumber, and you can do all the rest.

This leads to the problems worsening, and I end up having to hire an emergency technician to handle the repairs.

I definitely understand why you want them but you're better off hiring someone to manage in my opinon. 

In our property, the house was open to the air in the damp environment of coastal Florida, no heat or A/C at the house.  

I hire a property manager and I have never in 10+ years of having a PM had a tenant reach out to me, if they got upset or had a complaint they dealt with the property manager.

You always hire professional cleaners if it's an old person's home and construction cleaners if it's a disaster area.

& different parts of the asset can be depreciated on different schedules.To find out the useful lifespan of each component, you do a cost segregation study to analyze all of the parts.The raw land can't be depreciated so you start by giving that a value first.But other items can be depreciated on a quicker timeline.A roof, road, sidewalk, fencing, walls, gates, doors, latches, flooring, air conditioners, pavers, curbing, landscaping, etc.The IRS has a depreciation schedule for each type.Some parts are 5 yrs.