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

Instead, look at your major location-specific operating costs as an investor.

I am heavily invested into the stock market at the moment (Index Funds).

In fact, just finished one that I have yet to put on the market. 

I agree very market dependent. 

@Chelsea DiLuzio the Midwest markets are way different than the markets out west!

Your realtor should be the first source of guidance.For anyone here to provide you some guidance, you have to be more specific on the ask.There are always many things to consider when planning for different strategies.

Look at their marketing strategy.

If we were not able to raise the price of our homes by 20% or more we would had to stop.. my LORI plan started at 600k sold two of them and made our normal 100k net.. last loris I sold 36 months later went for 850 to 900k and we made right at 250k NET on those ones.. so it was very specific to plans that CASH buying empty nesters wanted ..

-why not pick a market closer to home?