Stay in school.

If they are staying and your current lease ended - then they automatically go on month to month and you can only increase the rent by 1.8% and you have to give them 90 days notice of that rent increase as well from the end of their term.  

His tech had been out there 4 hours trying to get the duct work to stay together. 

If she went to Assisted Living - I can help you but it's only KS Specific - each state is different but I'm guessing some of the guidelines carry across states in regards to how she will pay for the ALF and eligibility for Medicaid and Home and Community Based Services (which is a medicaid program that would help pay for ALF)Anyways in KS - in for someone to qualify for HCBS/Medicaid to help pay for their care either in the  home or assisted living - you need to have less than $2k in assets - and consistently less than $2k in the bank - there is also something called a 5 year lookback period - I do not 100% understand how the lookback period works but will soon enough.So - as far as the assets are concerned - if your friends mother has the house and any savings there is no way the govt will be paying for most of her stay in ALF - and I also think it would be difficult to house her in an ALF facility for $3k per month - can be done but tough - Due to no estate planning the family needs to decide on what they are going to do - they will either need to sell the house now and just pay her money down at the private pay rate in a facility until she "runs out of money" then apply for Medicaid and go from there or see if the strategy of renting the house with her present income will be enough to cover the facility she's staying at.Individually the systems are simple however there are so many moving parts to Medicaid HCBS I've discovered in my time as owner of a facility I can 100% understand the families frustrations. 

You are correct - if you don't stay for the two years there will be capital gains to be paid.

4) if your contractor will wait to get paid a few days after the draw must you will stay pay them upfront and show proof of this to lender before they will release funds back to you?

Stay well.

Unfortunately that will only help if the tenant either wants to stay or has decent credit and doesn't want to mess it up.

Guess I should stay away from this.

He should report issues with the property if they are a big deal and he may try to negotiate a longer term lease if he wants to stay long term.