I am all ears if anyone can lend some suggestions; however, after wasting thousands of dollars on DEV costs, I want to share my journey to help others.

Your point about long-term mindset really resonates with me; it’s crucial to consider how a property will perform over the years rather than just the initial cost.

My investments have been out of state but I'm starting to look at some local rehabs or new build projects.  

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).

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

Can't seem to reach anyone and clients aren't getting rehab draws.

I have a small house in Coleman you could start with, if you want to contribute the rehab.

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.