Are there specific tools, presentations, or approaches that help them feel more confident in taking that first step?

@Raiyan KhanYou can search these forums for vendor recommendations but you can also join a real estate investment club in the area you want to invest and get the same info.

Small talk, showing empathy, and expressing genuine interest in their situation can go a long way in establishing trust and goodwill.Be Willing to Walk AwayOne of the most powerful negotiating tools is the ability to walk away.

Quote from @Olivia Armstrong: Hey all, My husband and I have been searching for a property purchase, one that temporary checks our boxes and also kickstarts our investing journey.

I'm looking to purchase my first rental property and have been searching for a deal that would generate positive cash flow based on my projections.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Search for the BP podcast episode with Jude Bernard - he is very active in NYC.

To provide our buyers the greatest probability for success, we cast a wide net to evaluate ALL vacation rental prospects and narrow it down to the handful that meet the search criteria. 

I recommend searching "arbitrage" here and reading any/all of the hundreds of general threads about negative elements of arbitrage.

There will not be one PM covering all the places you mention in your post, so maybe refine your search a little, and then you can start interviewing.