You can always use a software like Turbo-Tax and follow the prompts.

If so, you can add package upsells automatically through your property management software (e.g.

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

Offering discounts for weekday or longer stays could also help improve occupancy.

Does anyone have any tips or software tools to help give estimates on pricing and the potential occupancy of the rental?

After which they invested $190k for $10800/year return or 5.6% (not even discounting for the 2.5 years to recover the initial negative equity).  

You’re paying too much for each 1/4 point discount.

Software developer - "What things do you look for in a CRM?"

You can get houses at huge discounts and it is a great time to buy for appreciation.

So, keep in mind this tax deduction is basically like getting a discount on the purchase.