We were heavily invested in the stock market and wanted to diversify. 

I've never heard of Kin, but I too am in the market for short term rental insurance.

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

Would love to connect with other investors in the area that are also doing long-term rentals, renovations, and/or short-term rentals.

Masthope had been rumored to be limiting STR, but it seems they are keeping their eye on the fallout after the big court win in Lake Ariel - https://www.timoneyknox.com/reversed-short-term-rental-regul...

As I dive into all the different paths I can take (single family vs multi-family, short term vs long term, cash flow vs appreciation, local vs out of state, etc..) my mind is scrambling and I've ended up doing nothing at all.I'm looking to join a mastermind that meets consistently and can really motivate one another to take our businesses to the next level. 

One key he found was mixing a welcoming atmosphere with firm guidelines.. it typically falls under standard tenant landlord laws for eviction.. so you’ll want to double-check local regulations.You mentioned Furnished Finders and Padslipt.com.. from what I’ve heard, those can be great if you’re targeting traveling professionals or short term visitors.

I recently purchased a Short Term rental property and plan to self manage the property.

There is no stock account that gives the leverage real estate does, at as low interest rate real estate does, at as low risk/ volatility real estate does. 

A rider allowing for using your owner-occupied property as a short-term rental for a specific/limited amount of time is very different than an investment property being used as a short or long term rental 100% of the time.Also, telling your home insurance company that you STR your home occasionally does not give you extra coverage for those types of risks, it simply means if your renter burns your home down the insurance company isn't going to immediately deny your claim.