Im ideally going to be starting my own property management company for small "boutique/aesthetic STR's" in the Lakes Region of NH. 

Easy to think about, hard to do.3) If would be advisable if you have money and access to money to cover items like expenses if the property doesn't cash flow well.  

She has since asked me to deduct the cost of her at-home test from her late rent fee and I refused as the lease states she is responsible for items in her unit costing less than $50.

No, because a) that might be their luxury/vice item for all I know, which is 100% fine if it's viewed as a luxury item that they just really personally enjoy and gain happiness from (it's much less harmful than other vices, like drugs or gambling!)

A property that has to be fully rehabed before renting it will in theory have a lower capex expense since you just replaced all the capex items.  

Those items may or may not be installed and if they break it's my choice to remove them and not install new ones because they are not part of the rent.

If you do inspections, it is for the purpose of identifying maintenance items.

@Tyler Wisner you have some good suggestions above but many "buy and hold" investors look for 3 method of income on investment properties:Appreciation of the Property - Meaning the local economy is strong enough to support a healthy housing marketPrinciple Buy Down - Meaning every payment your renter makes to you pays down the principle balance of the mortgageCash Flow - the amount of money you earn each month that is OVER and ABOVE your expenses on the propertyIf you find a market where you can have these 3 items you should be able to have a good market to invest in.  

Then, you put closing costs in your line items with your expenses and now you are saying that the $16k is not an expense.

Total scam........ they are often expensive, don't totally cover the items, the companies they use to "fix" claims are often crap and they will band aid the issue until the end of time......The single benefit is if you are OOS, you call them and they handle the claim, so you don't have to find your own repair people etc.....so its ease of use...... but you often have to manage the insurance company as they jerk you around, stall and band aid the actual issue.....Had one when I bought a rental in TX and then continued it when the initial expired..... regretted it to this day.I'll take one as part of the deal when I buy.... but wont keep paying for it myself.Better off building a network of repair companies you trust