You'll want to ask about their experience, read reviews, understand their availability, pricing, insurance / bonding, and how they safeguard their funds. 

I want to learn and get as much experience as I can.

If your new servicer wants to play games, file a complaint with the CFPB and dispute with the credit bureaus.

It wasn’t the biggest spread, but the experience was priceless.

Perhaps there is a relevant book or podcast that you could suggest to expand my knowledge in this area.Considering you're experience with creative finance deals, which you mentioned previously, I am keen to hear about your personal insights and experiences.

It's playing with plutonium.

It's a power play. 

Quote from @Dyllon Gibbs: Hi All,Does anyone have experience with rent guarantee insurance and any specific companies?

Others noted that the appreciation play could make it worth keeping, I tend to look more heavily on appreciation since real estate investing is more of a long term game.

I'd check local STR FB groups and see if you have a local Real Estate Club.You can offer your services there, maybe for free in exchange for the experience.