Understanding your long term goals is important in making a decision like this. 

Dennis,I like where your head is at trying to find tax strategies!

I had issues with renting out the place earlier, and the current rent doesn't cover even the mortgage interest, let alone other expenses like property tax, insurance etc.

Hi Prasit,To transition from agent to acquisition manager, here’s the quick path:Leverage Your Agent Skills: Use your market knowledge, negotiation experience, and connections to find and analyze deals—key acquisition manager skills.Wholesaling Experience (Optional): Wholesaling can help build your deal-finding and analysis skills, but it’s not necessary if you can transition directly using your agent background.Training: Consider certifications like CCIM for commercial real estate or courses on platforms like BiggerPockets to sharpen your acquisition expertise.Network: Connect with investors or real estate firms to gain insights and potential job opportunities in acquisitions.Let me know if you need help with financing as you move forward!

So, from that perspective, I like the idea of "involuntary conversion provisions" to not have to deal with increased "income" in 2023 (because of the insurance payments) and huge "expenses" in 2024 (because of paying the contractors).I thought that has nothing to do with CSS, partial dispositions, having to "retire" the old assets and start tracking the depreciation of the new assets (after all, the CSS allocated 5K to the old roof covering, and we paid 18K+ for the new roof).

A good rule - as long as the plumbing and electric has been updated, a well-built home from the mid-20th century is a better investment and will likely outlast a newer build.Credit to the respective author

It sounds like a cash-out refinance or a HELOC could work well for your situation.

It's like having lazy equity in any other asset.

If you would like to know further details .

With this kind of field its almost like all the info is out there but you dont know what to be looking at and in what order.