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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")

This ultimately why the $100k midwest single family homes are frequently discussed in these forums.....its what many are able to afford to buy.

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

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.

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. 

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

Its a tough subject because logically, they are joint and several guarantys so rationally a 100% guaranty from each of two people (one 740 one 680 for example) is ALWAYS going to be better than just one 100% guaranty from someone at 740 (so it wouldn't make sense to have a better rate for the latter)The problem is that there is fraud and "straw borrowers" out there where someone who is not involved in the property signs on to boost score and terms - so many DSCR Lenders in response either do the "non-rational" thing and price to the lower to avoid the fraud or use the higher of the two (and either be a little loose with things or just stay vigilant on any funny business)

Ultimately I wasn't able to contract anything.