I love Hospitable, but looking at Lodgify for their direct booking capability and customizable website templates.Does anyone use Stripe for online direct bookings?  

A lot of investors navigate this by using rental income to qualify rather than personal income.

Along with my 2 business partners I buy & build small micro-resorts and unique vacation rentals across the Appalachian region.

Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.

I currently own 3 properties, farm, rental, and private residence.

My second question is if I take most of the deprecation on the property in the first 5 years, is it in my best interest to purchase another rental property within those 5 years?

Complete a rental verification, but it should not be from any family member or an individual, request there last apartment, or property management company as a rental verification.

If so... do you make the guest take rental insurance or something? 

From what i've read online (not financial advice) the bank only requires one of the owners to use the property as their primary to qualify for a primary financing.From what I understand this will also very much depend on the internal guidelines of the particular lender you're talking to. 

A cost segregation study is a strategic tax planning tool that separates the assets that have a shorter useful life and can be depreciated over 5, 7 and 15 years from the residential rental property or nonresidential real property that are depreciated over 27.5 and 39 years, respectively.