With the new Fannie Mae 5% down payment conventional option on multi-family properties, I figured it might be possible to follow through with this strategy.

You don't do anything to hedge against the possibility of damages? 

While it is true with owning land and possible ADU in future, I have no plans to add any ADU and land is not important to me. 

What's up team, I have a subject to deal that I am working, and I want to make it as comfortable for the seller as possible.

An LLC would limit that, though not completely remove it as a possibility.

What do you think the best possible experience an investor can have that reduces the "sifting through sooo much information" problem, quickly plugs them into a model such as one you've built and ultimately produces a transaction? 

My biggest advice would be to take your time and do as much research as possible.

BiggerPockets also has a calculator you can use to analyze deals and I highly recommend you start this as soon as possible, even if you are not ready to buy.

I'll try to give as much detail as possible so sorry if this is a little long-winded.I have two potential partners who are looking to do a deal together to buy a 2-4 unit in Cleveland (B neighborhood or higher) where I am located.

So if someone where to buy a townhome/condo or one of those #B ADUs as an investment property, how would we know if a type 2 STR permit is possible to obtain?