Ski Leases: Looking at the short term rental policies it does not cover leases longer than 30 days, seeing as there is a market for this type of rental what are peoples experience with this for ~4 month terms, and has it worked for summer leases as well.?

I just had to provide list of equipment bathrooms parking  and hvac etc etc.. and pictures to back it up.land to building ratio  So I helped her through it and it worked out great for us.

It really helps me with a real 'picture' of step by step events.You're welcome!

Just be sure to carefully consider the financing costs and make sure your STR income can comfortably cover them.

I guess the purpose for this is to help fund community improvements and maintenance though it's a bit unusual since HOA fees and property taxes typically cover these.

Close on the property- Purchase a Home Owners Warranty to cover the HVAC. 

Quote from @Eric Prescott: Yes, I understand that appreciation often means less cash flow and good cash flow typically means weaker appreciation, but there is a sweet spot where there is decent appreciation and sufficient cash flow to cover expenses so that the property pays for itself, and that is what I'm honing in on. 

Insurance can be an issue as you would technically have to get it in the LLC's name and then you can have a personal umbrella to cover any overages. 

Is there any way to get PennyMac to lower the payoff amount, at least to just the principal amount, enough to cover the partial claim, satisfy the mortgage lender and be able to afford to relocate my family (I only need $7,000 to $10,000 to get a vehicle/uhual and move my family, and that includes the new place)?

It would be great to connect with those who have already covered some distance on a similar journey as well as those who are just starting!