We've had great tenants, a good property management company, and few expenses over the past few years.

Currently I use Foremost insurance but their prices have gone up somewhat significantly this year and I’m wondering if anyone has a good company/agent they like to use and would recommend as a place for me to start looking.

Regarding the LTC (loan to cost) this will vary depending on your funding source (bank, private equity, etc.).

Would the company in discussion here know how to do this?

This is often viewed as a "gift" so lenders place limits on the amount that can be "gifted" as well as the manner that these funds can be transferred to you. 

Right now you are the licensed, insured, have  o experience and if you work remotely off little in the way of hands on at a property.Honestly someone could hire a Virtual Assistant from a other country.I would try and build your resume by working for a company for now.

However I have done residential real estate deals in 13 states using various exit strategies and my main advantage for this project is that I own a GC company within range of the property with experience handling large scale projects.

There are "interest tracing rules", that can roughly be summarized as the interest on a loan is deductible as a business expense only if you use the funds for that business. 

We just bought a condo on the Gulf Coast, and the old management company has said the same snowbirds come to our unit every year from December 15- March 31.

A lot of people stifle their growth by using private lenders to fund 100% of the deal.