Nathan -It's understandable that you want to optimize your tax situation by strategically utilizing your capital losses.

.- It needed a community face lift and re-brand (was called windmill apartments....yuck.)We came in and strategically worked our business plan:- We upgraded the exterior including fresh paint, signage, and landscaping.- We removed delinquent tenants and changed the community standards around to provide a safe and clean place of living.- We've upgraded 75% of the units with fresh flooring, paint, cabinets, countertops, and appliances as needed.When we took over the property the 16 units were producing around $9000/month in gross rent.I just checked our rent roll today, and we just crossed $17,000 in gross income monthly!

It's essential to work with a knowledgeable real estate agent and tax advisor to ensure you are making informed and strategic investment decisions.

Given your situation and the market dynamics, buying a rental property to cash flow and build equity sounds like a strategic move.

Cashing out on your rental properties can be a strategic move to expand your portfolio.

As @Nicole Heasley started, you have to be very strategic and have an exit strategy in place before the interest kicks in.

They should be able to help you strategize what will work given your current situation and qualify you appropriately. 

I would make strategic investments around or near those new interchanges and bypasses.  

Value Investing: Identify undervalued properties with potential for appreciation, often through strategic renovations or upgrades.

Buy strategic lots in new subdivisions as they get to around 50% filled and let the lot value escalate.8.