House hacking (buying a multi-family property and renting out units while living in one) allows you to cover or reduce your living expenses while building equity.

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.?

If your spouse qualifies for the Real Estate Professional status, then it will cover both of you.

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

Tacky.Your power outlets and switch don't have covers in the pics.

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.

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. 

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. 

Open carry: might shy away buyers.Conceal carry: well, most situations with gun fire escalate to the point you can fire or find cover before you need to draw.I used to get called a "stoner" because a bunch of prepper shows said carry a lighter and i always had one at work.Guess who almost dehydrated and died next to 4 ponds soon after?