In a better market you might be able to use those things to get a better deal on commercial insurance but in the current market there won't be flexibility.On personal policies/1-4 unit rental dwelling policies there won't be any flexibility whatsoever unless it's something the company already has built into their guidelines/pricing.

If I book a room that will work for two people (i.e. with two beds) but only book for one person would we be able to change the reservation later to be able to share the room?

These are all private so someone had to include them, and then that person can pursue you for failure to comply.

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

And, if you find that person on the right day, you can make a deal that works for both.

Then visit the lender website and see if the have an REO section or try to find a person's name.

Basic recommendations- Deed of Trust-Personal Guarantee-Promissory note-JV agreement (to protect the lender from violating usury laws)-clear late fee schedule, cure period agreement-cross collateral if the subject property doesn't safely cover you with enough equity

I would hire another person that has construction and real estate background.Take your  annual Salary. 

Born and raised in Lake Arrowhead and personally own several STRs in Arrowhead, and own an insurance business where we specialize in hard to insure homes and STRs in the mountains!

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