DSCR is available for an LLC to use for purchase and cash out refis as long as you never plan to occupy the property yourself.

At a minimum, having viable plans in place for development will make these lots more marketable and valuable to potential builders when we have conversations. 

Your story proves that being in the game creates opportunities you can’t plan for.

A shorter minimum stay and dynamic pricing are great for attracting bookings during slower periods, though the trade-off with single-night weekend stays is definitely a balancing act.

Denver is a strong market with solid appreciation and plenty of opportunities, especially for strategies like house hacking and the BRRRR method.Your plan to start with FHA and house hacking is a great way to get your feet wet.

Sometimes the tenants plan on paying a month's rent at two places to allow a less-hectic move. 

What do you plan on doing with the puppies (once they are old enough to rehome-ie 6-8 weeks old)? 

A living trust I recommend for estate planning - that is all it does.

We plan to keep this property long-term as part of our portfolio and look for additional investing opportunities in the future.

It's really impossible to give you a direct answer on your question without knowing a lot more about your plans.