There was a special assessment done in June which required an extra payment for a month but no special assessment in the last two months

We did not want to risk the difficulty on getting tenants out in Minnesota.

I considered reaching out to the community college and asking for an enterprising business student who might need a little extra money and a letter of reference while he/she is learning real estate. 

there is no reason to be a hard *** - just let the guy stay a few extra days and charge him for those days.

The biggest flag was where you said your friend can't claim extra income due to visa restrictions. 

If I had the extra money and felt that down the road I’d still be able to recoup it either through rent, or during resale then I’d proceed.

Pro: Partners can bring something extra to the table, such as capital, connections, different prospective and project experience.

If you have access to a great deal flow and are being held back by capital, then I would say you can grow that extra $15k at a quicker pace than the $150-80 = $70/mo net opportunity cost cash flow.You can objectively calculate this with opportunity cost calculations, rate of returns you're seeing, and inflation numbers.

been living in a home with my wife for over 25 years... wife past away in 2018 went into financial difficulty around 2005 when her illness was getting worse so we got a home modification loan in her name only... which helped us from selling our home. since 2018 I am the estate executor and been paying for 3 years now.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!