My wife has never had a specific place in mind, so got to do my choice. 

There certainly may be some loss aversion that drove Tyler's choice.  

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")

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. 

He also tells the story of Steven Spielberg: the ultimate "fake it 'til you make it"!

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.

Nor took any action against 2 Trillion induced losses during GFC, by any banker or rating agency etc, but suppose it can't hurt to get some of your frustration out by filing a complaint, and the RADD managers may be dumb enough to give you back some of your money, as they purported to in 1 review (probably a lie).If I were in RADDs shoes today, I would have 2 choices, file bankruptcy and disperse assets after paying all liabilities, probably <50 cents on the dollar for investors, or do what they are doing, which is to go to church every day and pray for lower rates and tell the investors to go pound Sand. 

Ultimately I wasn't able to contract anything.