You"re bound to end up with tiny people or normal ones with low lasting power.

Left Field Investors is a powerful community of like-minded passive investors who vet and invest in syndications. 

I am in the same boat.  

House hacking is powerful and also not as challenging/scary as one may think.

Also just in terms of getting started I am jumping in pretty quickly with two houses.My question then is are those concerns worth powering through, being a little uncomfortable for the year and learning a lot? 

You need to show that you have staying power and understand the business.

you can include all those expenses (closing costs, improvements and/or repairs, any fees, points, sales price, etc) when calculating internal rate of return (IRR).Internal rate of return is a powerful metric because it can evaluate the return for all cash inflows/outflows over the life of your investment.

They have veto power on decision-making and help drive the train--investors already have the right to meet every so often and vote on things.Happy to chat off-line if you'd like.

It is very powerful and customizable.

I would research whether a life estate (either with powers or bare) accomplishes the goals here.