If we moved out and rented the main house as-is, we'd barely break even or even potentially enter negative cashflow.That's why the idea of renting out the ADU for extra income sounds appealing.

Does anyone have ideas of who to talk? 

Here's a list of FAQs to dive more in depth: https://www.biggerpockets.com/forums/51/topics/1113749-cost-...

Here are a few below:Generally, buying through your personal name can reduce the interest rate - commercial rates on LLC mortgages are usually higher but you can research thisMost LLCs on incorporation don’t have any credit so it may be difficult to find. a lenderIf you own the property in your personal name you are exposing yourself to more risk and will want to transfer the property into LLC as soon as you canIf you own property in your personal name and transfer to LLC the lender may not allow or can call the entire loanLLC or personal ownership you need insurance.If you search the forums for this topic using the magnifying glass feature in top right corner of your screen on BiggerPockets you will find a lot of discussion on "Quit Claim" "Buying through LLC", "LLC or not" etc....

I've started building a spreadsheet for myself and wanted a few examples for Ideas.

I would reply back "how can we put an offer in if we have no idea of the condition of the home".Are these properties that are listed on the market?  

Most people suggest finding an independent agent who can shop multiple carriers as the best option and that is a good idea also but know that some Indy agent's don't want investor business so I'll say it simply Indy's are great but not all Indy's want your business. 

Some ideas would be to: Take a look at a market report for Pittsburgh and add a few percentage points to be conservative, Call around to multifamily brokers or property managers in the area and ask their vacancy rate, asks banks what their vacancy assumption is for underwriting, etc...

Also I've been doing a lot of reading on this, but would love to hear any partnership structuring ideas and tips.

We're primarily interested in vacation rentals, but are always willing to listen to other ideas.