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.

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. 

If things start getting tight, you can always switch to doing work for clients too in order to raise funds. 

The Democratic bill proposed seems to offer funding to landlords while the Republican bills offers landlords nothing. 

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

That's the only real answer to make anything work in a place like Boston.And to answer your question on returns, 4x-20x leverage (including owner occupant loan options) + appreciation is what makes real estate a better investment the index funds and worth the hassle.

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).

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

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!

I don't know your area, so I can only write to my experiences in PA.You don't really convert your property to Section 8 (S8), but rather sign a lease with a tenant who happens to be funded by S8.