Ideally I wanted to live in Lake View as that's my dream neighborhood, but I just didn't have the funds/income.

He has stated clearly to me that he does not desire to be a RE investor.  

I am torn between pricing rent lower with a minimum 3 night stay or just weeding out the less desirable/more work clients with higher pricing.  

I like that, unlike with say trading for a hedge fund, I can create opportunities for others rather than solely line the pockets of someone richer (that being said I still intend to make money).

I have been funding these types of props since 2002 for a turnkey company in Detroit who used LA based sales agents then over the years I have met most all of the Marketing companies or they have sold clients of mine props I see the commish on my huds. 

Every investor has their own path, and hearing different perspectives will only enrich your journey.Challenges in Real Estate Investing:Finding deals: In competitive markets, it can be tough to find good deals that make sense financially.Capital and financing: Finding funding, especially as a new investor, can sometimes be challenging.Dealing with tenants: Managing rental properties and dealing with tenants can be tricky, especially with issues like late rent or property damage.Market risk: Real estate markets fluctuate, and external factors (like economic shifts or local development projects) can impact property values.I’d be happy to continue the conversation if you want to dive deeper into any of these topics!

How long do you think the Hedge fund is going to place more properties with that Servicer?

And I still finance land flippers all over the US.. so perk test and soil test we deal with every week on our funding's.

Another option would be working with private lenders to see if they're open to your idea should you need additional funding. 

In southern Florida I fund and profit / loss is 50/50.