If your place is in Hawaii, might want to check out the short-term rental regulations.

Its unfortunate but I rather be in line with city regulations.

Please note that there are specific rules and regulations that can be different depending on what city/county your property is located in.I would suggest that you look up joining either RHAWA or WLA. 

Plan is to partner with a few folks for the downpayment/liquidity requirement (planning on a hard money loan).All properties in the DC market, so rents should not soften too much due to federal government as main employer (one hopes), but I still want to stay on the conservative side given the unknown economic impacts of COVID-19.

Most investors like Chicago because of appreciation, high airbnb potential, easy airbnb city regulations and the ARV strategies for cashing out can be lucrative.

One would hope not but it is the government!

Most accountants I have spoken about this say that I shouldn't worry since the tax money that I'm collecting from a tenant to pay the government doesn't affect my bottom line since it's just taxes. 

What is the City of Denver government telling you?

Are you saying that you don't want to make $1M in sales simply because $300k or $400k of it goes to the government?

After that, what the document is calling a second & third mortgage for lesser amounts were issued.In the court documents, the defendants include the initial lender, as well as the other lien holders - the HOA, the local government, the US government, and the 2nd & 3rd mortgage lenders.It looks like the company issuing the  Lis Pendens bought / obtained the paper from the lender (what they are calling the 1st mortgage, but is really the second) and is the plaintiff in the case.I am guessing (unless the original amount was paid off) it is therefore a foreclosure by a junior interest.