However the owners retired and her team left when she sold the businesses.

End result here is that whether or not the new property was eligible for a 1031 exchange you were investing inside a qualified retirement account. 

Long distance investing/managing is an obvious for me since I move every couple years, but I retire from the Navy in 5-7 years, and I'll finally settle in one place. 

So either you pay for the repair out of the idle cash in your account, file an insurance claim and use those funds, or rollover/transfer funds from another retirement account to cover the cost. 

Overall goal being to retire in the home in 10-15 years.  

Or we gradually perform high-quality updates for a live-in flip, then roll the equity into a new home.Regarding rental income, we aim to boost income, lower our effective tax rate by generating more low tax-drag income with rental income (since there’s not much we can do to lower out W2 tax bills) and have retirement cash flow.To compare the financial impact over 10-20 years, we want to analyze renting versus flipping.

However, I am thinking of having my parents who are retired living there part of the year and doing STR for the remainder of the time.

Most local banks and credit unions will have free accounts.You need two accounts: checking and savings. 

Fortunately, he moved to FL after the sale, bought a mansion as his retirement home, and saved by the state's homestead laws.

In 1-2 years you could save enough to purchase a home to house hack.