This goal will enable our family to have a secure retirement plan, college (or business startup) funds and long term passive income to vacation and travel whenever we would like."

For a 4-plex condominium complex, I was paying $144/year per unit in 2019, now I am getting quotes that are $550/year per unit for identical units in same complex.2) Insurance providers such as State Farm have stopped taking new customers for landlord insurance, and companies such as Travellers have set limits of no more than 10 units per landlord.Has anyone else faced a similar situation?

Considering VRBO in Saint Pete to give us an excuse to travel more and add to the portfolio.

You could do vacation or as others do here, check the STR threads, rent to traveling healthcare professionals.

My job has allowed me to transition into a partially remote role which will require frequent travel back to Grand Rapids. 

Further, rising vaccination rates gave Americans more freedom to venture out to eat, attend a game, travel or engage in other activities they would have avoided at the height of the pandemic.

@Kevin HowardI used to do the manual checks, hut I started traveling more so this became problematic.

We are traveling there in two weeks and plan to stay for a week to explore the area and get a feel for neighborhoods. 

I own a town home there as a rental property, and I wanted to figure out what advice you could give me to classify my trips home as travel expenses to my property, especially when the main goal may be seeing my family for Christmas or other holidays/vacation weeks. 

In general it all comes down to "what are the primary drivers of short-term travel in an area" and OKC is not too hard to figure out.Medical, night on the town, home remodel, or visiting kids in the city . . . there are a few other draws, but them're the kickers.