And keep in mind that the rate on the 2nd lien will likely be 10-12% so depending on the cash flow it might not actually yield that much cash to you at closingMore importantly, it's just more debt so ultimately it sounds like you need an income-producing event to actually improve your situation and avoid some of the consequences that you mentioned

Much of this analysis is based on the size of the land, how much it will cost to do the horizontal development, and then estimate the cost of the vertical build and ultimate value (aka "sale price")

My ultimate goal is to house hack a 3–4 unit property.I’m seeking advice on how to accurately estimate the closing costs and monthly expenses associated with a multi-family property.

@Catherine Javier If you find the property is more of a liability to you and ultimately decide to sell, the 1031 exchange would probably be the best way to take advantage of using the tax and find something with a greater growth potential.

It's the ultimate "investor" property as it's designed for investors unlike some other condo or house in Carlsbad that you won't be able to visit because it will be on a 1-2 year lease and will only net you equity via appreciation, not cash.

Personal Timing.For many landlords contemplating a sale, the timing ultimately comes down to personal choice.

What Don says captures most deals that ultimately looked to have been undervalued by the market, or current owners, but really were not. 

As far as office I remain intrigued by it, also at least in our area condos have been brutally hit and I think offer a “deal” without quite the downsides to office, I tend to think office/retail in suburban and even pandemic boom markets (I’ve started investing on the eastern shore of Md and have considered some office deals there) offers the best risk/reward of office because you have a population boom coupled with ultimately still a low supply of office space, where as urban areas have lost population and have a huge glut of supply, I think the ultimate fate of a lot of urban office trends towards zero/land value. 

Looking to buy duplex to live in and ultimately renovate if the numbers make sense.

Ultimately I wasn't able to contract anything.