I assume that I don't actually have to pay the capital gains until the principal repayment exceeds my cost basis, which on an amortized loan would be quite awhile (assuming they don't refinance and pay me off altogether).

And STR is much more involved with high turnover rates so you’ll not only need to post the listing but know how to keep it competitive so that you maximize bookings, of course, furnishing it, keeping supplies, restocked, cleaning, maintenance, And what about consideration to any local STR rules and regulations?  

As long you clearly identify and track the expense per property (and you can do that in Quicken, with properties, categories and subcategories, or in Quickbooks), you’ll not need CCs and accounts per properties.Here are some graphical diagrams to help you on this quest (or confuse you further): - Asset Protection Decision Diagram - to help assess the need for asset protection, and what to implement: https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-decision-diagram - Asset Protection Onion Diagram - what, when, and at what cost one should implement in terms of asset protection - https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-onion-diagram-v2 - What is needed for complete asset protection OR the domains that need to be intersected to find asset protection

Next, what is the cost of the renovation vs higher rent delta? 

We're looking to branch out there for low-cost owner financing properties (offering financing for those renting). 

So, the family member is pocketing cash and guaranteeing a stable cost of living for themselves basically locking in their future at a time when values are high.

That makes a big difference on what is available for submetering, type of technology and cost.

@Paige Kehoe cost vs time will be your biggest challenge!

Even after you have title, if there is a redemption period in that state, then you want to wait until the redemption period has passed before you make any costly repairs or upgrades. 

Hello guysReno got costly on this last BRRRR deal.