It’s my brother and 2 good friends that have some experience. the money lender would be a family member of mine lending out of their self directed IRA so they will be lenient with us.

If I put my money in the S&P 500 index fund, the annual return is about 10%.

Doing a 75% 1st mortgage and 15% heloc or heloan would likely give you better cost of funds all around.If this is an investment property, you can do 80% cash out refi using NonQM loans such as DSCR loans, but at a higher cost/rate than if you stick with 75% loan to value. 

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

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).

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.

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!

Or do you want to be a part owner with a group of people like in a fund or syndication?

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

They come in with a different name usually acquired by buying out a small/mid company, wipe the market with unlimited funds backed by fed and big banks, dry the pool and leave when there is nothing left.