The LLC plan to avoid lawsuits is a construct from people who charge to set up LLC's which fails to tell you: annual fee for LLC filings, extra costs for extra tax returns, total need for an advisor CPA.

I know all this because recently a repair was done in both units, and the one apartment is nicely kept, and the other apartment is not nicely kept at all and they have an extra animal.

If you can pickup a $250k house with an extra bedroom you maybe in the $2k rent range. 

Pull all the equity out and get to a cash position.The extra money you made over the past year of exponential appreciation will offset your tax liability on the sale of the home.You never hold when the market is going to crash.We are headed into a strong correction in the market.Thanks

Without fanfare or extra unneeded words  

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

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.