I'm looking to not only share my experiences but also offer my services to those who might need them.

I suggest using a service like Mayistay.

I have had no issues with using their rent collection services. 

My Question is, for these up sales how do you expose these packages to the guests, are they included in your listing or added to the base price, if a guest chooses a package do they pay for the reservation how they would normally through the booking platform then pay for the package separately?

Our experience is that many lenders/servicer customer representatives may not know the protections that exist for those that want to put asset protection steps in place. 

Also, for flips, I like to reserve an additional 15-20% in contingency for unforeseen conditions or changes. 

If you did not like that experience, maybe you should try a smaller company to get a more personalized service experience.  

Is there a certain direct mail service they prefer?  

I keep a very healthy amount of reserves to avoid using my insurance unless I have a catastrophic issue.

Most people I know start with low money down programs so they can get away with a initial capital investment of around $25k but you also need reserves.