We are now doing short term rentals but we're thinking about changing to a small wedding venue. 

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?

They are exceedingly rare, thus very expensive, but I believe they represent an excellent long term steady income and store of value.  

Has anyone used bridge loans for this type of strategy or is there any other loans that anyone would recommend other than HELOC?

These should be reflected in the purchase price or negotiated as part of the terms, such as the seller carrying some of the renovation burden.Use seller financing to your advantage by proposing a price closer to $225,000-$250,000 with terms such as 20% down, a low interest rate (4-5%), or interest-only payments for 3-5 years, with a balloon payment once renovations are complete and cash flow stabilizes.If the seller is firm on price, consider negotiating higher down payment terms to reduce the financed amount, paired with interest-only terms or a price reduction tied to renovation milestones.Key questions to address include the condition of the septic system, which can be a significant expense if it fails.

Passive income is certainly the name of the game - building a real estate portfolio and creating generational wealth are key ingredients to long term holistic financial health and success.There are fantastic real estate investment opportunities in various markets, particularly in the Midwest and Southeast of the country. 

And you can do other things, rent, sell on terms, etc etc etc..

If we include investments in mortgage loans (trust deeds), real estate partnerships, REITs as well as direct property ownership, I’m at about 80%.  

With VA loans, you’ve got a huge advantage to get started with little to no money down, and military bases are perfect for long-term or short-term rentals.

We do a ton of them here in Chicago and everyone of them is a great long term success!