To pay for this, I used a heloc on my current home.

They filed an eviction on a tenant mid-escrow and withheld information on eviction until I saw a posted eviction notice on the door after closing.

There is virtually no reason to keep “cash” on hand for repairs. 

Congratulations on the upcoming wedding!

Here's some online software options that you commonly see recommended on BiggerPockets.

I was hoping to see a roadmap on how to go from $100k invested on the 1st STR and the strategy on acquiring a 2nd STR and so forth.

Here is a link that provides fantastic information on the turnkey investing option from BP. 

While you work on that, you could also explore creative financing options like DSCR loans or partnerships to fast-track your first STR.

Future enhancements include the planned Silver Line rail alignment with nearby stops, as well as potential commuter bus services, pedestrian paths, and bike lanes.The development benefits from proactive rezoning by the city, transitioning the land from industrial to mixed-use urban development.

Would a HELOC or home equity loan on my personal home be a good idea to fund this?