Downtown is a good landing spot for wedding parties, corporate groups, families during the holidays, events, etc.

Well it will need to be life changing events like having kids, new job, divorce, taking care family members etc but the rule of thumb is to live there for at least one year then being able to rent it out and converting it into an investment property.

Going to networking events to network with Realtors, Mortgage, Title etc all helps. 

I have included snippets of your message and my replies or comments in bold.What investor meetups I should attend- BP rules prevent posting outside events/meetups here.

within 5-30 minutes of 4 wedding venues and about 10 minutes from a military base that does training.

What happens if there is another COVID like event and STR use is banned for most of the year? 

A great way to start is by attending RE events and joining a local investors association.

I am attending the 3 day event in a couple weeks.

Has anyone tried to operate a business on a plot of land with minimal development until it builds revenue for a structure (flea-market, private park, outdoor event venue, etc)?

But then she explained that it's on a certain land that allows it to be used as a short term rental and that due to its location between within 2 months of the year (when huge events take place, every year) it would make enough to cover its mortgage for the year.