I’d say the best thing to do would be to perform a cost benefit analysis (CBA).

With 5+ units, while they of course review your personal ability, they put more emphasis on the cash flow of the property itself and how its ability to perform is of high importance to them.Always keep in mind the following: 1) market cycle; 2) debt; 3) exit strategy (h/t Bill Ham).As you’re already seeing with deal flow, we’re towards the top of the market cycle with valuation.

Secondly, a large majority of investors will try to boost cash flow by having their agent raise their deductibles but that is personal preference. 

You also need to know your local market and then you need to know how to properly and legally structure and perform the transaction.

Otherwise, I know some really solid DSCR lenders here in Colorado that have pretty nice rates currently. and since you have a track record of how the property performs you should have an easy time getting a loan on it. 

The home is to be in the same general condition as when the home inspection was performed. 

To perform a lot split on an existing lot with an already built home, the new bill allows requirements from individual municipalities to set minimum lot SF and layouts, there are utility easement issues, and most existing homeowners will not want to split their SF lot on their primary residence.

Even though our ex home has appreciated ~$2k/month over its 28 year hold and it now has a rent to purchase ratio of >1.5%, it is my worse performing property.  

However to answer your question there are lenders that will look more at the performance of the property than your own personal financial situation.

Sell the property at a large loss:Downside: Large loss shown on my tax return, potentially impacting ability to get future financing; Upside: I can redeploy some capital into higher performing projects immediately; After running the numbers on my side, it feels like it makes way more sense to sell the property at a large loss.