Sale of a condo with a tenant. Thoughts?

[Allen Lopez]

So I have a unit that I bought in April 2017 for $71k HOA FEES ARE $300/month. I immediately rented it out for $850/month with an AMAZING Tenant. He pays rent on time, keeps the place spotless, and never gives me any issues. In may of this year I was going to increase the rent but I gave him a chose to pay $50 more per month or if he signed a two year contract I would keep the rent at $850/month. He agreed to the two year contract. This year the property has increased in value and is now worth $95-100k based on other units in the same complex being sold. I would like to sale it (meaning I would get 90% of sale price after all the fees and everything). i have $95k from another unit i just sold (hoa fees there where $300/month), and i have another $60k saved up. Questions: 1) should I sale? If I sale, I would put all the money together and instead buy a house ($200-250k with HOA fees at $150/quarter). Rent of the area where I am thinking is between $1500-2000/month. 2) can i sale with the tenant inside? I the tenant and I dont want him to lose his home (he has earn My respect). 3) can i ask more since I already have the tenant inside for two years?