A duplex or triplex could be a solid first step.Get Legal AdviceTalk to a trusted attorney before agreeing to anything like a trust.

I've only owned a couple sfh am middle-aged and not sure I agree with flipping sfh at this point to create wealth, time freedom and passive income so I have been reading and there seems to be a lot of talk with multi-families and more specifically apartment investing.

By sending a check, in many states, if the tenant cashes the check they are de facto agreeing with your damage assessment and will have little ground to dispute your accounting.  

I agree: Pitch deck to a specific deal is the ultimate goal, but in the mean time, I need something to just show lenders, potential investors and others in the industry so it sounds like we know what we're talking about.

Agreed with Jonathan.

Quote from @Johnny Lynum: Absolutely agree!

He is out of Chicago, but I believe he can cover all across the country.

I agree with @John Underwood that if you can get separates then do that.

Now, the owner can vet the operator one time, offload routine maintence to the operator, and receive the rent they've agreed to in the lease, possibly for years to come.

We have been working to save up to purchase a primary residence (in Boston or the surrounding suburbs), however, since Massachusetts is currently one of the most expensive housing markets in the country, I’m wondering if it would be more beneficial to purchase my first investment property (out-of-state) first (instead of waiting for home prices to hopefully drop a little in Mass).2.