Find out their goals (current and post sale), desired timeline for selling/moving, where they'd like to move to next (if owner occupied), reason(s) for not already selling to an investor or with a Realtor, Plan B if they're unable to sell within the desired timeframe.let's say they've got a property that needs work and they're interested in selling.

That’s just the truth but all isn’t lost:- Created actionable steps, Created a system that can actually produce the desired outcome.

It sounds like it's not in a very desirable area, based on the price and rents.

Main questions should ask about the seller's:- Reasons/Motivations for wanting to sell- Desired timeline to close- Plan's after selling (relocation, reinvesting proceeds, 1031 exchange, etc)- Back-up plan in case they are unable to sell within the desired timeline- Reasons for not already selling to/with a investor or RealtorAdditional questions will depend on the type of seller lead i.e. pre-foreclosure, probate, fsbo, absentee owner, etc.Here is an example of a youtube search you can use to begin finding call recordings.There are 1,000s and you'll find that the best/most effective ones don't even sound like sales calls.

That area is desirable and will most likely have negative cash flow for a while.

The best way to estimate expenses is experience and knowledge of your specific asset type and market.For vacancy, that will depend on your market and the quality/desirability of your type of unit.

There are multiple planned developments currently in the works that would expand the desire for vacation homes, but as of now, we're still waiting for that to occur Hi Stetson, we are now considering building a new home. could you please recommend a spot builder in Cape Coral?

With a strong desire to learn, I’m focused on acquiring the skills needed to make strategic investments and build generational wealth through real estate.I’m is eager to dive into the fundamentals of the industry, from property evaluation to cash flow management, and is excited to learn from the experienced mentors and peers.Welcome to the community!

My goals currently are to help him get to a state where he can live the life he desires.  

Your thesis is basically rent low and accept less desirable tenants so I don't think that is the best thesis to base an investment off.