Questions for expanded my business

[Martin Goodenberger]

Hello, first time poster and would appreciate some feedback on a few areas of concern as I look to expand my buy and hold portfolio.  I currently own 2 multi family properties in Portland (ME). The first started as a house hack, but is now fully rented. Both houses are currently held in traditional mortgages and have 3 units each. One of the properties is actually split with a friend of mine - both our names are on the mortgages and our two families have split the expenses and profits 50/50.  

After extensive renovation, both properties are cash flowing >$1500/mo.  Hence, my desire to get more properties. I have ~$150K to invest and some potential investors that could contribute $50K each. I'm not really sure how to approach such a setup, though.

I previous looked at going the LLC route on the 2nd property that I bought with a partner, but it was more trouble than it was worth. I was able to find a mortgage, but I struggled to find insurance.  Only one guy would return my call.  The cost was more than 3X the cost with my current insurance on a similar property and the guy sounded inconvenienced the entire time we spoke.  From reading here, I believe an LLC structure is the right next step (if I'm going to accept contributions from other FAF type investors), but where do you go for commercial insurance?

Secondly, I would appreciate any advice on structuring the payouts and % ownership.  To make it simple, let's say I own 50% and 2 others own 25% each.  I was thinking that some of the monthly gross would be held in the LLC's name to cover repairs and other expenses (please tell me if this isn't normal). Then, when money is paid out to investors, should I ensure this happens equally by % to keep people's ownership % constant? Or allow them to withdraw funds (monthly or quarterly) and immediately recalculate % ownership? I would like an approach that is fair to current investors, but also encourages them to let some of the funds rid for future investments. If I keep money in and they don't, then their % ownership will (albeit very slowly) be diluted continuously.

In addition to using the cash flow of the LLC's first investment to save up for new purchases, I'd like the flexibility to add new investors. Do I simply sell 'shares' whenever someone (that I've vetted) wants to enter?  Or should I try to find a pool of investors large enough to get the next property and create a new LLC each time? Obviously, expectations would be set up front with the initial investors. 

Lastly...where to go for additional funding? I think the approaches above have ruled out any kind of conventional mortgage, so I'm left with commercial loans/private lenders. From what I've read around here, it sounds like getting funding for long term buy and hold will be more difficult than flips or sub-5 year investments. I've also read that approaching local banks should probably be my first step. I've seen some info posted about companies like RealtyShares, which might be an option. Do the eReit type companies invest in people like me, to add to their portfolio? Anything else I should consider? I'm open to setting an exit plan at ~10 years instead of 15-20(buy the investor out, sell or convert to condos & sell), but anything less is throwing away a lot of excellent cash flow from my POV.

Any suggestions would be appreciated.  Thanks.