Quote from @Matthew Paul: Earn more money , spend more money .

Just closed on this, and it's the final piece in my plan for a career shift. 

Planning ahead and staying financially disciplined now will set you up for successful growth in the years to come.

if a seller is not workable over the phone, we do not load up in our cars to go spend the day with total strangers that have pie in the sky daydreams a buckets full of cash from the sale of their house.

If you are going to do a flip, do a live in flip with the plan of living there for 2 years to sell tax free.

If yours is the only STR within 20 miles and there aren't any cities or larger towns within a 20-30 minute drive, you could easily run into trouble even finding a reliable cleaning person, let alone a full-service STR management company.I would also definitely take the time to find some comps on Airbnb in the same area as yours, with as close to the same bed/bath count as yours, and with the same finishes and amenities as you are planning to put in yours.  

I'd probably lean towards just increasing the rent a bit more than you originally planned and only for new tenants, require a deposit.

Way more that what you might spend on a monthly basis.

This is a good lesson for future tax planning.

The key to success in real estate investing lies in thorough research, strategic planning, and a willingness to adapt to changing market conditions.