@Charlie Martin Buying under an LLC offers liability protection and separates business finances, but it can complicate financing with higher rates and stricter terms, and lenders may still require a personal guarantee, impacting your DTI.For your first property, consider purchasing in your personal name for better loan terms and transferring it to an LLC later if needed, while using strong umbrella insurance to mitigate risk.

Also, be sure to consult a CPA about the timing of transitioning properties to an LLC to avoid potential complications with financing or taxes.Take time to compare multiple lenders and products that fit your strategy.

It is complicated because these investments are long-term, illiquid and completely out of your control.  

Not all that complicated, really. 

I am having difficulty finding a lender who can match a loan type as the single family seems to be complicating things.

Land development can seem complicated, but breaking it down step by step makes it much easier to manage.

Frankly I think too many people try and "automate" everything with technology that they complicate things so much that it is hard to manage.Remember you will get older folks staying and they might not want to try and use a tablet.I agree with Michael. 

@Joel Bayer- I stopped using the BRRRR calculator a while ago because it doesn't handle complicated financing scenarios like this well. 

You're essentially buying into a partnership with your friend with the partnership owning and operating the property.Now, the financial side of that gets more complicated and would generally include an advanced proforma/financial model that includes a GP/LP equity waterfall schedule that is based on how you and your friend agree that you will pay her and also share the profits.I assume that won't make sense to you right now, but I'll send you a DM.

How many folks with complicated entity structures sign contracts containing broad obligations to indemnify and hold harmless don’t even read the language because “it is standard”.