"Everyone" won't have their rents raised.

I now work from home doing a little accounting on the side while raising our children, but make no where near what I once made.  

If you go to these events leave all your credit cards at home.

Most taxing jurisdictions will reassess periodically (every year or two or three) and recent sales will come up and be used to raise (rarely lower) the assessment.Assume taxes will be based on the higher of (1) your purchase price or (2) the existing taxes when creating an investment pro-forma. 

Before we became investors, at the time it was rented, he was just happy to have someone in the home, so much so that he only asked for 3/4 of the actual mortgage as rent, but eventually he raised the rent to where he is now just breaking even - just getting the mortgage paid.He is adamant that he just wants to get the tenant to purchase the property. 

Lots not raised in years

She is willing to raise her clients contract to 98K, put 20% down of 98K to me.

I didn’t raise $25 per year, instead, I have been raising rent from $50 to $150 each unit on existing tenants per year without any problem.  

Do they have late payments, or have they just maxed a $500 credit card? 

I definitely would not do a 2yr lease, that is less attractive to you than 1yr not more, and I certainly would NOT offer or agree (handshake or otherwise) to not raise the rent at the end of that year.